Francis Albert Sinatra
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Francis Albert Sinatra (; December 12, 1915 – May 14, 1998) was an American singer and actor. Nicknamed the "Chairman of the Board" and "Ol' Blue Eyes", he is regarded as one of the most popular entertainers of the 20th century. Sinatra is among the
world's best-selling music artists The following list of best-selling music artists includes musical artists from the 20th century to the present with claims of 75 million or more record sales worldwide. The sales figures are calculated based on the formula detailed below. The ...
, with an estimated 150 million record sales globally. Born to Italian immigrants in
Hoboken, New Jersey Hoboken ( ; ) is a City (New Jersey), city in Hudson County, New Jersey, Hudson County in the U.S. state of New Jersey. Hoboken is part of the New York metropolitan area and is the site of Hoboken Terminal, a major transportation hub. As of the ...
, Sinatra began his musical career in the swing era and was influenced by the easy-listening vocal style of
Bing Crosby Harry Lillis "Bing" Crosby Jr. (May 3, 1903 – October 14, 1977) was an American singer, comedian, entertainer and actor. The first multimedia star, he was one of the most popular and influential musical artists of the 20th century worldwi ...
. He joined the
Harry James Harry Haag James (March 15, 1916 – July 5, 1983) was an American musician who is best known as a trumpet-playing band leader who led a big band to great commercial success from 1939 to 1946. He broke up his band for a short period in 1947, but ...
band as the vocalist in 1939 before finding success as a solo artist after signing with
Columbia Records Columbia Records is an American reco ...
in 1943, becoming the idol of the " bobby soxers". In 1946, Sinatra released his debut album, '' The Voice of Frank Sinatra''. He then signed with
Capitol Records Capitol Records, LLC (known legally as Capitol Records, Inc. until 2007), and simply known as Capitol, is an American record label owned by Universal Music Group through its Capitol Music Group imprint. It was founded as the first West Coast-base ...
and released several albums with arrangements by
Nelson Riddle Nelson Smock Riddle Jr. (June 1, 1921 – October 6, 1985) was an American arranger, composer, bandleader and orchestrator whose career stretched from the late 1940s to the mid-1980s. He worked with many vocalists at Capitol Records, including ...
, notably ''
In the Wee Small Hours ''In the Wee Small Hours'' is the ninth studio album by American singer Frank Sinatra, released on April 25, 1955, by Capitol Records. Produced by Voyle Gilmore with arrangements by Nelson Riddle, the album's songs deal with themes such as i ...
'' (1955) and '' Songs for Swingin' Lovers!'' (1956). In 1960, Sinatra left Capitol Records to start his own record label,
Reprise Records Reprise Records is an American record label founded in 1960 by Frank Sinatra. It is owned by Warner Music Group, and operates through Warner Records, one of its flagship labels. Artists currently signed to Reprise Records include Green Day, En ...
, releasing a string of successful albums. He collaborated with
Count Basie William James "Count" Basie (; August 21, 1904 – April 26, 1984) was an American jazz pianist, organist, bandleader, and composer. In 1935, he formed the Count Basie Orchestra, and in 1936 took them to Chicago for a long engagement and the ...
on '' Sinatra-Basie: An Historic Musical First'' (1962) and '' It Might as Well Be Swing'' (1964). In 1965, he recorded '' September of My Years'' and starred in the
Emmy The Emmy Awards, or Emmys, are an extensive range of awards for artistic and technical merit for the television industry. A number of annual Emmy Award ceremonies are held throughout the year, each with their own set of rules and award catego ...
-winning television special '' Frank Sinatra: A Man and His Music''. After releasing '' Sinatra at the Sands'' in 1966, Sinatra recorded one of his most famous collaborations with
Tom Jobim Tom or TOM may refer to: * Tom (given name), including a list of people and fictional characters with the name. Arts and entertainment Film and television * ''Tom'' (1973 film), or ''The Bad Bunch'', a blaxploitation film * ''Tom'' (2002 film) ...
, ''
Francis Albert Sinatra & Antonio Carlos Jobim ''Francis Albert Sinatra & Antonio Carlos Jobim'' is a 1967 album by Frank Sinatra and Antônio Carlos Jobim. The tracks were arranged and conducted by Claus Ogerman, accompanied by a studio orchestra. Along with Jobim's original compositions, t ...
''. It was followed by 1968's '' Francis A. & Edward K.'' with
Duke Ellington Edward Kennedy "Duke" Ellington (April 29, 1899 – May 24, 1974) was an American Jazz piano, jazz pianist, composer, and leader of his eponymous Big band, jazz orchestra from 1924 through the rest of his life. Born and raised in Washington, D ...
. Sinatra retired in 1971 following the release of "
My Way "My Way" is Paul Anka's English-language lyrical adaptation of the French song " Comme d'habitude", released by Frank Sinatra in 1969. The original song was written by Jacques Revaux, Gilles Thibaut, and Claude François, and was first recor ...
" but came out of retirement two years later. He recorded several albums and released "
New York, New York New York, often called New York City (NYC), is the List of United States cities by population, most populous city in the United States, located at the southern tip of New York State on New York Harbor, one of the world's largest natural harb ...
" in 1980. Sinatra also forged a highly successful acting career. After winning the
Academy Award for Best Supporting Actor The Academy Award for Best Supporting Actor is an award presented annually by the Academy of Motion Picture Arts and Sciences (AMPAS). It has been awarded since the 9th Academy Awards to an actor who has delivered an outstanding performance in ...
for ''
From Here to Eternity ''From Here to Eternity'' is a 1953 American romantic Drama (film and television)#War drama, war drama film directed by Fred Zinnemann and written by Daniel Taradash, based on the 1951 From Here to Eternity (novel), novel of the same name by J ...
'' (1953), he starred in ''
The Man with the Golden Arm ''The Man with the Golden Arm'' is a 1955 American independent drama film noir directed by Otto Preminger, based on the novel of the same name by Nelson Algren. Starring Frank Sinatra, Eleanor Parker, Kim Novak, Arnold Stang and Darren Mc ...
'' (1955) and ''
The Manchurian Candidate ''The Manchurian Candidate'' is a novel by Richard Condon, first published in 1959. It is a political thriller about the son of a prominent U.S. political family who is brainwashed into being an unwitting assassin for a communist conspiracy. T ...
'' (1962). Sinatra also appeared in musicals such as '' On the Town'' (1949), ''
Guys and Dolls ''Guys and Dolls'' is a musical theater, musical with music and lyrics by Frank Loesser and book by Jo Swerling and Abe Burrows. It is based on "The Idyll of Miss Sarah Brown" (1933) and "Blood Pressure", which are two short stories by Damon Run ...
'' (1955), ''
High Society High society, sometimes simply Society, is the behavior and lifestyle of people with the highest levels of wealth, power, fame and social status. It includes their related affiliations, social events and practices. Upscale social clubs were open ...
'' (1956), and '' Pal Joey'' (1957), which won him a
Golden Globe Award The Golden Globe Awards are awards presented for excellence in both international film and television. It is an annual award ceremony held since 1944 to honor artists and professionals and their work. The ceremony is normally held every Janua ...
. Toward the end of his career, he frequently played detectives, including the title character in ''
Tony Rome ''Tony Rome'' is a 1967 American neo-noir mystery crime thriller film directed by Gordon Douglas and starring Frank Sinatra in the title role, alongside Jill St. John, Sue Lyon and Gena Rowlands. It was adapted from Marvin H. Albert's novel ...
'' (1967). Sinatra received the Golden Globe Cecil B. DeMille Award in 1971. On television, '' The Frank Sinatra Show'' began on
CBS CBS Broadcasting Inc., commonly shortened to CBS (an abbreviation of its original name, Columbia Broadcasting System), is an American commercial broadcast television and radio network serving as the flagship property of the CBS Entertainme ...
in 1950, and he continued to make appearances on television throughout the 1950s and 1960s. Sinatra was recognized at the
Kennedy Center Honors The Kennedy Center Honors are annual honors given to those in the performing arts for their lifetime of contributions to Culture of the United States, American culture. They have been presented annually since 1978, culminating each December in ...
in 1983, awarded the
Presidential Medal of Freedom The Presidential Medal of Freedom is the highest civilian award of the United States, alongside the Congressional Gold Medal. It is an award bestowed by decision of the president of the United States to "any person recommended to the President ...
in 1985, and received the
Congressional Gold Medal The Congressional Gold Medal is the oldest and highest civilian award in the United States, alongside the Presidential Medal of Freedom. It is bestowed by vote of the United States Congress, signed into law by the president. The Gold Medal exp ...
in 1997. Sinatra received eleven
Grammy Awards The Grammy Awards, stylized as GRAMMY, and often referred to as The Grammys, are awards presented by The Recording Academy of the United States to recognize outstanding achievements in music. They are regarded by many as the most prestigious a ...
, including the Grammy Trustees Award,
Grammy Legend Award The Grammy Legend Award, or the Grammy Living Legend Award, is a special award of merit given to recording artists by the Grammy Awards, a music awards ceremony that was established in 1958. Honors in several categories are presented at the ceremo ...
, and the
Grammy Lifetime Achievement Award The Grammy Lifetime Achievement Award is a special Grammy Award The Grammy Awards, stylized as GRAMMY, and often referred to as The Grammys, are awards presented by The Recording Academy of the United States to recognize outstanding achiev ...
. American music critic
Robert Christgau Robert Thomas Christgau ( ; born April 18, 1942) is an American music journalist and essayist. Among the most influential music critics, he began his career in the late 1960s as one of the earliest professional rock critics and later became a ...
called him "the greatest singer of the 20th century" and he continues to be regarded as an iconic figure.


Early life

Francis Albert Sinatra was born on December 12, 1915, in a tenement at 415 Monroe Street in
Hoboken, New Jersey Hoboken ( ; ) is a City (New Jersey), city in Hudson County, New Jersey, Hudson County in the U.S. state of New Jersey. Hoboken is part of the New York metropolitan area and is the site of Hoboken Terminal, a major transportation hub. As of the ...
, the only child of
Italian Italian(s) may refer to: * Anything of, from, or related to the people of Italy over the centuries ** Italians, a Romance ethnic group related to or simply a citizen of the Italian Republic or Italian Kingdom ** Italian language, a Romance languag ...
immigrants Natalina "Dolly" Garaventa and Antonino Martino "Marty" Sinatra. Sinatra weighed at birth and had to be
delivered ''Delivered'' is a 1998 crime comedy film directed by Guy Ferland and written by Andrew Liotta and Lawrence Trilling. The film stars Ron Eldard, David Strickland, Leslie Stefanson, Scott Bairstow, and Nicky Katt Agustín Islas Katt (May 11 ...
with the aid of
forceps Forceps (: forceps or considered a plural noun without a singular, often a pair of forceps; the Latin plural ''forcipes'' is no longer recorded in most dictionaries) are a handheld, hinged instrument used for grasping and holding objects. Forcep ...
, which caused severe scarring to his left cheek, neck, and ear, and perforated his eardrum—which remained damaged for the rest of his life. His grandmother resuscitated him by running him under cold water until he gasped. Due to his injuries, his baptism at St. Francis Church in Hoboken was delayed until April 2, 1916. A childhood operation on his
mastoid The mastoid part of the temporal bone is the posterior (back) part of the temporal bone, one of the bones of the skull. Its rough surface gives attachment to various muscles (via tendons) and it has openings for blood vessels. From its borders, t ...
bone left major scarring on his neck, and during adolescence he was further scarred by cystic acne. Sinatra was raised in the
Catholic Church The Catholic Church (), also known as the Roman Catholic Church, is the List of Christian denominations by number of members, largest Christian church, with 1.27 to 1.41 billion baptized Catholics Catholic Church by country, worldwid ...
. Sinatra's mother was energetic and driven; biographers believe that she was the dominant factor in the development of her son's personality and self-confidence. Sinatra's fourth wife Barbara would later claim that Dolly "knocked him around a lot" when he was a child. Dolly became influential in Hoboken and in local Democratic Party circles. She worked as a
midwife A midwife (: midwives) is a health professional who cares for mothers and Infant, newborns around childbirth, a specialisation known as midwifery. The education and training for a midwife concentrates extensively on the care of women throughou ...
, and according to Sinatra biographer
Kitty Kelley Katherine Kelley (born April 4, 1942) is an American journalist and author of best-selling unauthorized biographies of Jacqueline Kennedy Onassis, Elizabeth Taylor, Frank Sinatra, Nancy Reagan, the British royal family, the Bush family, and O ...
, ran an illegal abortion service that catered to Italian Catholic girls, for which she was nicknamed "Hatpin Dolly". She had a gift for languages and served as a local interpreter. Sinatra's illiterate father was a
bantamweight Bantamweight is a weight class in combat sports and weightlifting. For boxing, the range is above and up to . In kickboxing, a bantamweight fighter generally weighs between . In mixed martial arts, MMA, bantamweight is . The name for the class ...
boxer who later worked at the Hoboken Fire Department, working his way up to captain. Due to his illiteracy, he stressed the importance of a "complete and full" education and had instilled in his son the desire to become a civil engineer and enroll at
Stevens Institute of Technology Stevens Institute of Technology is a Private university, private research university in Hoboken, New Jersey. Founded in 1870, it is one of the oldest technological universities in the United States and was the first college in America solely de ...
in Hoboken. Sinatra spent much time at his parents' tavern in Hoboken, working on his homework and occasionally singing for spare change. During the
Great Depression The Great Depression was a severe global economic downturn from 1929 to 1939. The period was characterized by high rates of unemployment and poverty, drastic reductions in industrial production and international trade, and widespread bank and ...
, Dolly provided money to her son for outings with friends and to buy expensive clothes, resulting in neighbors describing him as the "best-dressed kid in the neighborhood". Excessively thin and small as a child and young man, Sinatra's skinny frame later became a staple of jokes during stage shows.''Sinatra at the Sands'' (1966),
Reprise Records Reprise Records is an American record label founded in 1960 by Frank Sinatra. It is owned by Warner Music Group, and operates through Warner Records, one of its flagship labels. Artists currently signed to Reprise Records include Green Day, En ...
At a young age, Sinatra developed an interest in music, particularly
big band A big band or jazz orchestra is a type of musical ensemble of jazz music that usually consists of ten or more musicians with four sections: saxophones, trumpets, trombones, and a rhythm section. Big bands originated during the early 1910s and ...
jazz and listened to
Gene Austin Lemeul Eugene Lucas (June 24, 1900 – January 24, 1972), better known by his stage name Gene Austin, was an American singer and songwriter, one of the early " crooners". His recording of " My Blue Heaven" sold over 5 million copies and was for ...
,
Rudy Vallée Hubert Prior Vallée (July 28, 1901 – July 3, 1986), known professionally as Rudy Vallée, was an American singer, saxophonist, bandleader, actor, and entertainer. He was the first male singer to rise from local radio broadcasts in New York Ci ...
, Russ Colombo, and
Bob Eberly Robert Eberly (born Robert Eberle; July 24, 1916 – November 17, 1981) was an American big band vocalist best known for his association with Jimmy Dorsey and his duets with Helen O'Connell. His younger brother Ray was also a big-band singer, m ...
while idolizing
Bing Crosby Harry Lillis "Bing" Crosby Jr. (May 3, 1903 – October 14, 1977) was an American singer, comedian, entertainer and actor. The first multimedia star, he was one of the most popular and influential musical artists of the 20th century worldwi ...
. For his 15th birthday, his uncle Domenico gave him a
ukulele The ukulele ( ; ); also called a uke (informally), is a member of the lute (ancient guitar) family of instruments. The ukulele is of Portuguese origin and was popularized in Hawaii. The tone and volume of the instrument vary with size and con ...
, with which he performed at family gatherings. Sinatra attended David E. Rue Jr. High School from 1928, and A. J. Demarest High School (since renamed as Hoboken High School) in 1931, where he arranged bands for school dances, but left without graduating after having attended only 47 days before being expelled for "general rowdiness". To please his mother, he enrolled at Drake Business School, but departed after 11 months. Dolly found her son work as a delivery boy at the ''Jersey Observer'' newspaper (since merged into ''
The Jersey Journal ''The Jersey Journal'' was a daily newspaper, published from Monday through Saturday, covering news and events throughout Hudson County, New Jersey. ''The Journal'' is a sister paper to ''The Star-Ledger'' of Newark, ''The Times'' of Trenton a ...
''), where his godfather Frank Garrick worked; he later worked as a riveter at the Tietjen and Lang shipyard. He began performing in local Hoboken social clubs and sang for free on radio stations such as
WAAT Waat is a village in the Nyirol County of Jonglei State, in the Greater Upper Nile region of South Sudan South Sudan (), officially the Republic of South Sudan, is a landlocked country in East Africa. It is bordered on the north by Sudan; ...
in Jersey City. In New York, Sinatra found jobs singing for his supper or for cigarettes. To improve his speech, he began taking
elocution Elocution is the study of formal speaking in pronunciation, grammar, style, and tone as well as the idea and practice of effective speech and its forms. It stems from the idea that while communication is symbolic, sounds are final and compel ...
lessons for a dollar each from vocal coach John Quinlan, one of the first people to notice his impressive vocal range.


Music career


1935–1942: Hoboken Four, Harry James, and Tommy Dorsey

Sinatra began singing professionally as a teenager. He never learned to read music but learned by ear. He got his first break in 1935 when his mother persuaded a local singing group called the 3 Flashes to let him join.
Baritone A baritone is a type of classical music, classical male singing human voice, voice whose vocal range lies between the bass (voice type), bass and the tenor voice type, voice-types. It is the most common male voice. The term originates from the ...
Fred Tamburro stated that "Frank hung around us like we were gods or something", admitting that they only took him on board because he owned a car and could chauffeur the group. Sinatra soon learned they were auditioning for the ''
Major Bowes Amateur Hour The ''Major Bowes Amateur Hour'' was an American radio talent show broadcast in the 1930s and 1940s, created and hosted by Edward Bowes (1874–1946). Selected performers from the program participated in touring vaudeville performances, under ...
'' show and "begged" the group to let him join. With Sinatra, the group became known as the "Hoboken Four" and passed an audition from
Edward Bowes Edward Bowes (June 14, 1874 – June 13, 1946), professionally known as Major Edward Bowes, was an American radio personality of the 1930s and 1940s whose '' Major Bowes Amateur Hour'' was the best-known amateur talent show on radio during its ...
to appear on the show. They each earned $12.50, and attracted 40,000 votes to win first prize—a six-month contract to perform on stage and radio across the U.S. Sinatra quickly became the group's lead singer, and, much to the jealousy of his fellow group members, garnered most of the attention from the girls. Due to the success of the group, Bowes kept asking for them to return, disguised under different names, varying from "The Secaucus Cockamamies" to "The Bayonne Bacalas," although this may be apocryphal, sourced from Sinatra’s humorous stage patter during his legendary appearance with the Count Basie orchestra at the Sands (1966). In 1938, Sinatra found employment as a singing waiter at a roadhouse called "The Rustic Cabin" in
Englewood Cliffs, New Jersey Englewood Cliffs is a borough in Bergen County, in the U.S. state of New Jersey. As of the 2020 United States census, the borough's population was 5,342, an increase of 61 (+1.2%) from the 2010 census count of 5,281, which in turn reflected a ...
, for which he was paid $15 a week. The roadhouse was connected to the WNEW radio station in New York City, and he began performing with a group live during the ''Dance Parade'' show. Despite the low salary, Sinatra felt that this was the break he was looking for, and boasted to friends that he was going to "become so big that no one could ever touch him". In March 1939, saxophone player Frank Mane, who knew Sinatra from Jersey City radio station WAAT, arranged for him to audition and record " Our Love", his first solo studio recording. In June, bandleader
Harry James Harry Haag James (March 15, 1916 – July 5, 1983) was an American musician who is best known as a trumpet-playing band leader who led a big band to great commercial success from 1939 to 1946. He broke up his band for a short period in 1947, but ...
, who had heard Sinatra sing on "Dance Parade", signed him to a two-year contract of $75 a week after a show at the Paramount Theatre in New York. It was with the James band that Sinatra released his first commercial record "From the Bottom of My Heart" in July. No more than 8,000 copies were sold, and further records released with James through 1939, such as "
All or Nothing at All "All or Nothing at All" is a song composed in 1939 by Arthur Altman, with lyrics by Jack Lawrence. Frank Sinatra recording Frank Sinatra's August 31, 1939 recording of the song, accompanied by Harry James and his Orchestra was a huge hit in 19 ...
", also had weak sales on their initial release. Thanks to his vocal training, Sinatra could now sing two tones higher, and developed a repertoire which included songs such as " My Buddy", "
Willow Weep for Me "Willow Weep for Me" is a popular song composed in 1932 by Ann Ronell, who also wrote the lyrics. The song form is AABA, written in time,Zimmers, Tighe, E. (2009). ''Tin Pan Alley Girl: A Biography of Ann Ronell''. McFarland. pp. 19-22. alth ...
", " It's Funny to Everyone but Me", "Here Comes the Night", "
On a Little Street in Singapore "On a Little Street in Singapore" is a jazz song written by Peter DeRose and Billy Hill (songwriter), Billy Hill. It had some measure of popularity in the 1930s and 1940s, marked by a number of high-profile performances. Artists to cover the song ...
", " Ciribiribin", and "Every Day of My Life". Sinatra became increasingly frustrated with the Harry James band, feeling that he was not achieving the major success and acclaim he was looking for. His pianist and close friend
Hank Sanicola Henry William "Hank" Sanicola (14 June 1914 – 6 October 1974) was an American music manager, publisher, businessman and pianist, best known for his work and association with Frank Sinatra from the late 1930s to the early 1960s. Early life Sanic ...
persuaded him to stay with the group, but in November 1939 he left James to replace Jack Leonard as the lead singer of the
Tommy Dorsey Thomas Francis Dorsey Jr. (November 19, 1905 – November 26, 1956) was an American jazz trombone, trombonist, composer, conductor and bandleader of the big band era. He was known as the "Sentimental Gentleman of Swing" because of his smooth-to ...
band. Sinatra earned $125 a week, appearing at the Palmer House in
Chicago Chicago is the List of municipalities in Illinois, most populous city in the U.S. state of Illinois and in the Midwestern United States. With a population of 2,746,388, as of the 2020 United States census, 2020 census, it is the List of Unite ...
, and James released Sinatra from his contract. On January 26, 1940, he made his first public appearance with the band at the Coronado Theatre in
Rockford, Illinois Rockford is a city in Winnebago County, Illinois, Winnebago and Ogle County, Illinois, Ogle counties in the U.S. state of Illinois. Located in far northern Illinois on the banks of the Rock River (Mississippi River tributary), Rock River, Rockfor ...
, opening the show with " Stardust". Dorsey recalled: "You could almost feel the excitement coming up out of the crowds when the kid stood up to sing. Remember, he was no
matinée idol Matinée idol is a term used mainly to describe film or theatre stars who are adored to the point of adulation by their fans. The term almost exclusively refers to adult male actors. Matinée idols often tend to play romantic and dramatic ...
. He was just a skinny kid with big ears. I used to stand there so amazed I'd almost forget to take my own solos". Dorsey was a major influence on Sinatra and became a
father figure A father figure is usually an older man, normally one with power, authority, or strength, with whom one can identify on a deeply psychology, psychological level and who generates emotions generally felt towards one's father. Despite the literal t ...
. Sinatra copied Dorsey's mannerisms and traits, becoming a demanding perfectionist like him, even adopting his hobby of toy trains. He asked Dorsey to be godfather to his daughter Nancy in June 1940. Sinatra later said that "The only two people I've ever been afraid of are my mother and Tommy Dorsey." Though Kelley says that Sinatra and drummer
Buddy Rich Bernard "Buddy" Rich (September 30, 1917 – April 2, 1987) was an American jazz drummer, songwriter, conductor, and bandleader. He is considered one of the most influential drummers of all time. Rich was born and raised in Brooklyn, New York, ...
were bitter rivals, other authors state that they were friends and even roommates when the band was on the road, but professional jealousy surfaced as both men wanted to be considered the star of Dorsey's band. Later, Sinatra helped Rich form his own band with a $25,000 loan and provided financial help to Rich during times of the drummer's serious illness. In his first year with Dorsey, Sinatra recorded more than forty songs. Sinatra's first vocal hit was the song " Polka Dots and Moonbeams" in late April 1940. Two more chart appearances followed with "Say It" and "
Imagination Imagination is the production of sensations, feelings and thoughts informing oneself. These experiences can be re-creations of past experiences, such as vivid memories with imagined changes, or completely invented and possibly fantastic scenes ...
", which was Sinatra's first top-10 hit. His fourth chart appearance (and his first on the first officially published ''Billboard'' chart) was "
I'll Never Smile Again "I'll Never Smile Again" is a 1939 song which became a 1940 ''Billboard'' chart-topper by Tommy Dorsey written by Ruth Lowe. It has been recorded by many other artists since, becoming a jazz and pop standard. The most successful and best-know ...
", topping the charts for twelve weeks beginning in mid-July. Other records with Tommy Dorsey issued by
RCA Victor RCA Records is an American record label owned by Sony Music Entertainment, a subsidiary of Sony Group Corporation. It is one of Sony Music's four flagship labels, alongside Columbia Records (its former longtime rival), Arista Records and Epic ...
include " Our Love Affair" and "Stardust" in 1940; " Oh! Look at Me Now", " Dolores", " Everything Happens to Me", and "
This Love of Mine "This Love of Mine" is a popular Great American Songbook, American song that was first recorded in 1941 by Tommy Dorsey and His orchestra, with a vocal by Frank Sinatra. Frank Sinatra, Sinatra wrote the words and Sol Parker and Hank Sanicola wrote ...
" in 1941; " Just as Though You Were There", " Take Me", and "
There Are Such Things "There Are Such Things" is a popular song by Stanley Adams, Abel Baer, and George W. Meyer, published in 1942. The first and most popular version of the song was performed by Tommy Dorsey's orchestra with vocals by Frank Sinatra and The Pied ...
" in 1942; and " It Started All Over Again", " In the Blue of Evening", and " It's Always You" in 1943. As his success and popularity grew, Sinatra pushed Dorsey to allow him to record some solo songs. Dorsey eventually relented, and on January 19, 1942, Sinatra recorded " Night and Day", " The Night We Called It a Day", "
The Song is You "The Song Is You" is a jazz standard composed by Jerome Kern with lyrics by Oscar Hammerstein II. It was written for their musical '' Music in the Air'' (1932) and sung in that show by Tullio Carminati. In the subsequent 1934 film, the song was re ...
", and " Lamplighter's Serenade" at a Bluebird recording session, with
Axel Stordahl Axel Stordahl (August 8, 1913 – August 30, 1963) was an American arranger and composer who was active from the late 1930s through the 1950s. He is perhaps best known for his work with Frank Sinatra in the 1940s at Columbia Records. With his ...
as arranger and conductor. Sinatra first heard the recordings at the
Hollywood Palladium The Hollywood Palladium is a theater (building), theater located at 6215 Sunset Boulevard in the Hollywood, Los Angeles, Hollywood neighborhood of Los Angeles, California, United States. It was built in a Streamline Moderne, Art Deco style and ...
and Hollywood Plaza and was astounded at how good he sounded. Stordahl recalled: "He just couldn't believe his ears. He was so excited you almost believed he had never recorded before. I think this was a turning point in his career. I think he began to see what he might do on his own". After the 1942 recordings, Sinatra believed he needed to go solo, with an insatiable desire to compete with
Bing Crosby Harry Lillis "Bing" Crosby Jr. (May 3, 1903 – October 14, 1977) was an American singer, comedian, entertainer and actor. The first multimedia star, he was one of the most popular and influential musical artists of the 20th century worldwi ...
, but he was hampered by his contract which gave Dorsey 43% of Sinatra's lifetime earnings. A legal battle ensued, eventually settled in August 1942. On September 3, 1942, Dorsey bade farewell to Sinatra, reportedly saying "I hope you fall on your ass", but he was more gracious on the air when replacing Sinatra with singer
Dick Haymes Richard Benjamin Haymes (September 13, 1918 – March 28, 1980) was an Argentine singer, songwriter and actor. He was one of the most popular male vocalists of the 1940s and early 1950s. He was the older brother of Bob Haymes, an actor, televi ...
. Rumors began spreading in newspapers that Sinatra's mobster godfather,
Willie Moretti Guarino "Willie" Moretti (February 24, 1894 – October 4, 1951), also known as Willie Moore, was an Italian-American mobster who served as underboss of the Genovese crime family and top member of New Jersey faction under the administration of ...
, coerced Dorsey at gunpoint to let Sinatra out of his contract for a few thousand dollars. Sinatra persuaded Stordahl to come with him and become his personal arranger, offering him $650 a month, five times his salary from Dorsey. Dorsey and Sinatra, who had been very close, never reconciled their differences.


1942–1945: Onset of Sinatramania and Role in World War II

By May 1941, Sinatra topped the male singer polls in ''
Billboard A billboard (also called a hoarding in the UK and many other parts of the world) is a large outdoor advertising structure (a billing board), typically found in high-traffic areas such as alongside busy roads. Billboards present large advertis ...
'' and ''
DownBeat ''DownBeat'' (styled in all caps) is an American music magazine devoted to "jazz, blues and beyond", the last word indicating its expansion beyond the jazz realm that it covered exclusively in previous years. The publication was established in 1 ...
'' magazines. His appeal to bobby soxers, as teenage girls of that time were called, revealed a new audience for popular music, which had previously been recorded mainly for adults. The phenomenon became officially known as "Sinatramania" after his "legendary opening" at the Paramount Theatre in New York on December 30, 1942. According to Nancy Sinatra,
Jack Benny Jack Benny (born Benjamin Kubelsky; February 14, 1894 – December 26, 1974) was an American entertainer who evolved from a modest success as a violinist on the vaudeville circuit to one of the leading entertainers of the twentieth century with ...
later said, "I thought the goddamned building was going to cave in. I never heard such a commotion... All this for a fellow I never heard of." Sinatra performed for four weeks at the theatre, his act following the
Benny Goodman Benjamin David Goodman (May 30, 1909 – June 13, 1986) was an American clarinetist and bandleader, known as the "King of Swing". His orchestra did well commercially. From 1936 until the mid-1940s, Goodman led one of the most popular swing bi ...
orchestra, after which his contract was renewed for another four weeks by Bob Weitman due to his popularity. He became known as "Swoonatra" or "The Voice", and his fans "Sinatratics". They organized meetings and sent masses of letters of adoration, and within a few weeks of the show, some 1,000 Sinatra fan clubs had been reported across the US. Sinatra's publicist, George Evans, encouraged interviews and photographs with fans and was the man responsible for depicting Sinatra as a vulnerable, shy, Italian–American with a rough childhood who made good. When Sinatra returned to the Paramount in October 1944, only 250 persons left the first show, and 35,000 fans left outside caused a near riot, known as the Columbus Day Riot, outside the venue because they were not allowed in. Such was the bobby-soxer devotion to Sinatra that they were known to write Sinatra's song titles on their clothing, bribe hotel maids for an opportunity to touch his bed, and steal clothing he was wearing, most commonly his
bow tie The bow tie or dicky bow is a type of neckwear, distinguishable from a necktie because it does not drape down the shirt placket, but is tied just underneath a winged collar. A modern bow tie is tied using a common shoelace knot, which is also ...
. Sinatra signed with
Columbia Records Columbia Records is an American reco ...
as a solo artist on June 1, 1943, during the
1942–44 musicians' strike Year 194 ( CXCIV) was a common year starting on Tuesday of the Julian calendar. At the time, it was known as the Year of the Consulship of Septimius and Septimius (or, less frequently, year 947 ''Ab urbe condita''). The denomination 194 for thi ...
. Columbia Records re-released Harry James and Sinatra's August 1939 version of "All or Nothing at All", which reached number 2 on June 2 and was on the best-selling list for 18 weeks. He initially had great success, and performed on the radio on ''
Your Hit Parade ''Your Hit Parade'' is an American radio and television music program that was broadcast from 1935 to 1953 on radio, and seen from 1950 to 1959 on television. It was sponsored by American Tobacco's Lucky Strike cigarettes. During its 24-year r ...
'' from February 1943 until December 1944, and on stage. Columbia wanted new recordings of their growing star as quickly as possible, so
Alec Wilder Alexander Lafayette Chew Wilder (February 16, 1907 – December 24, 1980) was an American composer and author. Biography Wilder was born in Rochester, New York, United States, to a prominent family; the Wilder Building downtown (at the "Four ...
was hired as an arranger and
conductor Conductor or conduction may refer to: Biology and medicine * Bone conduction, the conduction of sound to the inner ear * Conduction aphasia, a language disorder Mathematics * Conductor (ring theory) * Conductor of an abelian variety * Cond ...
for several sessions with a vocal group called the Bobby Tucker Singers. Of the nine songs recorded during these sessions, seven charted on the best-selling list. That year he made his first solo nightclub appearance at New York's
Riobamba Riobamba (, full name San Pedro de Riobamba; Quechua: ''Rispampa'') is the capital of Chimborazo Province in central Ecuador, and is located in the Chambo River Valley of the Andes. It is located south of Ecuador's capital Quito and situated at ...
, and a successful concert in the Wedgewood Room of the prestigious Waldorf-Astoria New York that year secured his popularity in New York high society. Sinatra released "
You'll Never Know "You'll Never Know", sometimes referred to as "You'll Never Know (Just How Much I Love You)" in later years, is a popular song with music written by Harry Warren and the lyrics by Mack Gordon. The song is based on a poem written by a young Okla ...
", " Close to You", " Sunday, Monday, or Always" and " People Will Say We're in Love" as singles. By the end of 1943, he was more popular in a ''DownBeat'' poll than Bing Crosby. Sinatra did not serve in the military during World War II. On December 11, 1943, he was officially classified 4-F ("Registrant not acceptable for military service") by his draft board because of his perforated eardrum. However, Army files reported that Sinatra had actually been rejected because he was "not acceptable material from a psychiatric viewpoint;" his emotional instability was hidden to avoid "undue unpleasantness for both the selectee and the induction service". Briefly, there were rumors reported by columnist
Walter Winchell Walter Winchell (April 7, 1897 – February 20, 1972) was a syndicated American newspaper gossip columnist and radio news commentator. Originally a vaudeville performer, Winchell began his newspaper career as a Broadway reporter, critic and c ...
that Sinatra paid $40,000 to avoid military service, but the FBI found this to be without merit. Toward the end of the war, Sinatra entertained the troops during several successful overseas
USO The United Service Organizations Inc. (USO) is an American nonprofit-charitable corporation that provides live entertainment, such as comedians, actors and musicians, social facilities, and other programs to members of the United States Armed F ...
tours with comedian
Phil Silvers Phil Silvers (born Phillip Silver; May 11, 1911 – November 1, 1985) was an American entertainer and comedic actor, known as "The King of Chutzpah". His career as a professional entertainer spanned nearly 60 years. He achieved major popularity w ...
. During one trip to Rome, he met
the Pope The pope is the bishop of Rome and the visible head of the worldwide Catholic Church. He is also known as the supreme pontiff, Roman pontiff, or sovereign pontiff. From the 8th century until 1870, the pope was the sovereign or head of sta ...
, who asked him if he was an operatic tenor. Sinatra worked frequently with the popular
Andrews Sisters The Andrews Sisters were an American close harmony singing group of the swing and boogie-woogie eras. The group consisted of three sisters: contralto LaVerne Sophia Andrews (1911–1967), soprano Maxene Anglyn Andrews (1916–1995), and mezz ...
in radio in the 1940s, and many USO shows were broadcast to troops via the
Armed Forces Radio Service The American Forces Network (AFN) is a government television and radio broadcast service the United States Armed Forces provides to soldiers stationed or assigned overseas, and is headquartered at Fort Meade in Maryland. AFN comprises two sub ...
(AFRS). In 1944, Sinatra released " I Couldn't Sleep a Wink Last Night" as a single and recorded his own version of Irving Berlin's " White Christmas". The following year he released " I Dream of You (More Than You Dream I Do)", " Saturday Night (Is the Loneliest Night of the Week)", "
Dream A dream is a succession of images, ideas, emotions, and sensation (psychology), sensations that usually occur involuntarily in the mind during certain stages of sleep. Humans spend about two hours dreaming per night, and each dream lasts around ...
", and "
Nancy (with the Laughing Face) "Nancy (with the Laughing Face)" is a song composed in 1942 by Jimmy Van Heusen, with lyrics by Phil Silvers, called, originally, "Bessie (With The Laughing Face)". It was originally recorded by Frank Sinatra in 1944. Many, perhaps most, people ...
" as singles.


1946–1952: Columbia years and career slump

Despite being heavily involved in political activity in 1945 and 1946, in those two years, Sinatra sang on 160 radio shows, recorded 36 times, and shot four films. By 1946, he was performing on stage up to 45 times a week, singing up to 100 songs daily, and earning up to $93,000 a week. In 1946, Sinatra released "
Oh! What it Seemed to Be "Oh! What it Seemed to Be" is a song composed by Bennie Benjamin, George Weiss and Frankie Carle. The song was most popular in 1946, and was taken to number 1 that year by both Frank Sinatra and the Frankie Carle orchestra, the latter with Marjo ...
", " Day by Day", "
They Say It's Wonderful "They Say It's Wonderful" is a popular song written by Irving Berlin for the musical '' Annie Get Your Gun'' (1946), where it was introduced by Ethel Merman and Ray Middleton. A film version in 1950 again featured the song when it was performed ...
", "
Five Minutes More "Five Minutes More" is a 1946 American pop song written by Sammy Cahn (lyrics) and Jule Styne (music). It is sometimes referred to as "Give Me Five Minutes More". It was featured in the movie ''Sweetheart of Sigma Chi'', sung by Phil Brito, and w ...
", and "
The Coffee Song "The Coffee Song" (occasionally subtitled "They've Got an Awful Lot of Coffee in Brazil") is a novelty song written by Bob Hilliard and Dick Miles, first recorded by Frank Sinatra in 1946. Later that year it was recorded by The Smart Set, and by ...
" as singles, and launched his first album, '' The Voice of Frank Sinatra'', which reached No. 1 on the ''Billboard'' chart. William Ruhlmann of AllMusic wrote that Sinatra "took the material very seriously, singing the love lyrics with utter seriousness" and that his "singing and the classically influenced settings gave the songs unusual depth of meaning." He was soon selling 10million records a year. Such was Sinatra's command at Columbia that his love of conducting was indulged with the release of the set '' Frank Sinatra Conducts the Music of Alec Wilder'', an offering unlikely to appeal to Sinatra's core fanbase of teenage girls at the time. The following year he released his second album, '' Songs by Sinatra'', featuring songs of a similar mood and tempo such as
Irving Berlin Irving Berlin (born Israel Isidore Beilin; May 11, 1888 – September 22, 1989) was a Russian-born American composer and songwriter. His music forms a large part of the Great American Songbook. Berlin received numerous honors including an Acade ...
's "
How Deep is the Ocean? "How Deep Is the Ocean?" is a popular song written by Irving Berlin in 1932. The song was developed from an earlier Berlin song "To My Mammy" which was sung by Al Jolson in his film '' Mammy'' (1930). In the earlier song, the lyrics include the qu ...
" and
Harold Arlen Harold Arlen (born Hyman Arluck; February 15, 1905 – April 23, 1986) was an American composer of popular music, who composed over 500 songs, a number of which have become known worldwide. In addition to composing the songs for the 1939 film ' ...
's and
Jerome Kern Jerome David Kern (January 27, 1885 – November 11, 1945) was an American composer of musical theatre and popular music. One of the most important American theatre composers of the early 20th century, he wrote more than 700 songs, used in over ...
's "
All The Things You Are "All the Things You Are" is a song composed by Jerome Kern with lyrics written by Oscar Hammerstein II. The song was written for the musical '' Very Warm for May'' (1939)Mam'selle "Mam'selle" is a bittersweet song about a ''rendez-vous'' with a "mam'selle" ('' mademoiselle'') in a small café. The music was written by Edmund Goulding, the lyrics by Mack Gordon. Background The song originally appeared in the movie, ''The Raz ...
", composed by
Edmund Goulding Edmund Goulding (20 March 1891 – 24 December 1959) was a British screenwriter and film director. As an actor early in his career he was one of the 'Ghosts' in the 1922 silent film '' Three Live Ghosts'' alongside Norman Kerry and Cyril Chadwic ...
with lyrics by
Mack Gordon Mack Gordon (born Morris Gittler; June 21, 1904 – February 28, 1959) was an American lyricist for the stage and film. He was nominated for the best original song Oscar nine times in 11 years, including five consecutive years between 1940 and 1 ...
for the film ''
The Razor's Edge ''The Razor's Edge'' is a 1944 novel by W. Somerset Maugham. It tells the story of Larry Darrell, an American pilot traumatized by his experiences in World War I, who sets off in search of some transcendent meaning in his life. Maugham is th ...
'' (1946), was released as a single. Sinatra had competition; versions by
Art Lund Arthur Lund (April 1, 1915 – May 31, 1990) was an American baritone singer, initially with bandleaders Benny Goodman and Harry James, and was also a television and theatre, stage actor. Biography Arthur Lund was a graduate of Eastern Kent ...
,
Dick Haymes Richard Benjamin Haymes (September 13, 1918 – March 28, 1980) was an Argentine singer, songwriter and actor. He was one of the most popular male vocalists of the 1940s and early 1950s. He was the older brother of Bob Haymes, an actor, televi ...
,
Dennis Day Dennis Day (born Owen Patrick Eugene McNulty; May 21, 1916 – June 22, 1988) was an American actor, comedian and singer. He was of Irish descent. Early life Day was born and raised in the Throggs Neck Clason Point section of Bronx in New Yor ...
, and The Pied Pipers also reached the top ten of the ''Billboard'' charts. In December, he recorded "
Sweet Lorraine "Sweet Lorraine" is a popular song with music by Cliff Burwell and words by Mitchell Parish that was published in 1928 and has become a jazz standard. It is written in F major and has an AABA structure. A version by Teddy Wilson charted in Octo ...
" with the
Metronome All-Stars The Metronome All-Stars were a collection of jazz musicians assembled for studio recordings by ''Metronome Magazine'', based on its readers' polls. The studio sessions were held in the years 1939–42, 1946–53, and 1956, and typically consisted ...
, featuring talented jazz musicians such as
Coleman Hawkins Coleman Randolph Hawkins (November 21, 1904 – May 19, 1969), nicknamed "Hawk" and sometimes "Bean", was an American jazz tenor saxophonist.Yanow, Scot"Coleman Hawkins: Artist Biography" AllMusic. Retrieved December 27, 2013. One of the first ...
,
Harry Carney Harry Howell Carney (April 1, 1910 – October 8, 1974) was a jazz saxophonist and clarinettist who spent over four decades as a member of the Duke Ellington Orchestra. He played a variety of instruments, but primarily used the baritone saxophon ...
and
Charlie Shavers Charles James Shavers (August 3, 1920 – July 8, 1971) was an American jazz trumpeter who played with Dizzy Gillespie, Nat King Cole, Roy Eldridge, Johnny Dodds, Jimmie Noone, Sidney Bechet, Midge Williams, Tommy Dorsey, and Billie Holiday. He ...
, with
Nat King Cole Nathaniel Adams Coles (March 17, 1919 – February 15, 1965), known professionally as Nat King Cole, alternatively billed as Nat "King" Cole, was an American singer, jazz pianist, and actor. Cole's career as a jazz and Traditional pop, pop ...
on piano, in what Charles L. Granata describes as "one of the highlights of Sinatra's Columbia epoch". Sinatra's third album, ''
Christmas Songs by Sinatra ''Christmas Songs by Sinatra'' is the third studio album by the American singer Frank Sinatra. It was released on October 4, 1948 as a 78 rpm album set of four 78 rpm records in an actual album and as a 10" LP record (CL 6019) featuring a colle ...
'', was originally released in 1948 as a 78rpm album set, and a 10" LP record was released two years later. When Sinatra was featured as a priest in ''
The Miracle of the Bells ''The Miracle of the Bells'' is a 1948 American drama film directed by Irving Pichel, written by Quentin Reynolds and Ben Hecht, and produced by RKO. It stars Fred MacMurray, Alida Valli, Frank Sinatra and Lee J. Cobb. The film is based on the 1 ...
'', due to press negativity surrounding his alleged Mafia connections at the time, it was announced to the public that Sinatra would donate his $100,000 in wages from the film to the
Catholic Church The Catholic Church (), also known as the Roman Catholic Church, is the List of Christian denominations by number of members, largest Christian church, with 1.27 to 1.41 billion baptized Catholics Catholic Church by country, worldwid ...
. By the end of 1948, Sinatra had slipped to fourth on ''DownBeat''s annual poll of most popular singers, and in the following year he was pushed out of the top spots in polls for the first time since 1943. '' Frankly Sentimental'' (1949) was panned by ''DownBeat'', who commented that "for all his talent, it seldom comes to life." Though "
The Hucklebuck "The Hucklebuck" (sometimes written "The Huckle-Buck") is a jazz and R&B dance tune first popularized by Paul Williams and His Hucklebuckers in 1949. The composition of the tune was credited to Andy Gibson, and lyrics were later added by Roy ...
" reached the top ten, it was his last single release under the Columbia label. Sinatra's last two albums with Columbia, '' Dedicated to You'' and '' Sing and Dance with Frank Sinatra'', were released in 1950. Sinatra would later feature a number of the ''Sing and Dance with Frank Sinatra'' album's songs, including " Lover", "
It's Only a Paper Moon "It's Only a Paper Moon" is a popular music, popular song published in 1933 with music by Harold Arlen and lyrics by Yip Harburg and Billy Rose. Background It was originally titled "If You Believed in Me", but later went by the more popular ti ...
", and " It All Depends on You", on his 1961 Capitol release, ''
Sinatra's Swingin' Session!!! ''Sinatra's Swingin' Session!!!'' is the nineteenth studio album by Frank Sinatra, released on January 3, 1961. Six of the tracks on the album are re-recordings of a batch of songs that Sinatra had previously recorded on the Columbia album, ...
''. Culminating the low of his career was the death of publicist George Evans in January 1950. According to
Jimmy Van Heusen James Van Heusen (born Edward Chester Babcock; January 26, 1913 – February 6, 1990) was an American composer. He wrote songs for films, television, and theater, and won an Emmy and four Academy Award for Best Original Song, Academy Awards for ...
, Sinatra's close friend and songwriter, Evans's death to him was "an enormous shock which defies words", as he had been crucial to his career and popularity with the " Bobby soxers". Sinatra's reputation continued to decline as reports broke in February of his affair with Ava Gardner and the destruction of his marriage to Nancy, though he insisted that his marriage had long been over even before he met Gardner. In April, Sinatra was engaged to perform at the
Copa Copa or COPA may refer to: COPA COPA may refer to: * Child Online Protection Act, a former U.S. law to protect minors from certain material on the internet * Canadian Owners and Pilots Association * Cirrus Aircraft, Cirrus Owners and Pilots Asso ...
club in New York, but had to cancel five days of the booking due to a submucosal hemorrhage of the throat. Evans once said that whenever Sinatra suffered from a bad throat and loss of voice it was always due to emotional tension, which "absolutely destroyed him". In financial difficulty following his divorce and career decline, Sinatra was forced to borrow $200,000 from Columbia to pay his back taxes after MCA refused to front the money. Rejected by Hollywood, he turned to
Las Vegas Las Vegas, colloquially referred to as Vegas, is the most populous city in the U.S. state of Nevada and the county seat of Clark County. The Las Vegas Valley metropolitan area is the largest within the greater Mojave Desert, and second-l ...
and made his debut at the
Desert Inn The Desert Inn, also known as the D.I., was a hotel and casino on the Las Vegas Strip in Paradise, Nevada, which operated from April 24, 1950, to August 28, 2000. Designed by architect Hugh Taylor and interior design by Jac Lessman, it was the ...
in September 1951, and also began singing at the Riverside Hotel in
Reno, Nevada Reno ( ) is a city in the northwest section of the U.S. state of Nevada, along the Nevada–California border. It is the county seat and most populous city of Washoe County, Nevada, Washoe County. Sitting in the High Eastern Sierra foothills, ...
. Sinatra's decline in popularity was evident in his concert appearances. At a brief run at the Paramount in New York, he drew small audiences. At the Desert Inn in Las Vegas, he performed to half-filled houses. At a concert at
Chez Paree The Chez Paree was a Chicago nightclub known for its glamorous atmosphere, elaborate dance numbers, and top entertainers. It operated from 1932 until 1960 in the Streeterville neighborhood of Chicago at 610 N. Fairbanks Court. The club was the ep ...
in Chicago, only 150 people turned up in a 1,200-seat venue. By April 1952, he was performing at the Kauai County Fair in Hawaii. Sinatra's relationship with Columbia Records was disintegrating, with A&R executive
Mitch Miller Mitchell William Miller (July 4, 1911 – July 31, 2010) was an American choral conductor, record producer, record-industry executive, and professional oboist. He was involved in almost all aspects of the industry, particularly as a conductor ...
claiming he "couldn't give away" Sinatra records. Though several notable recordings were made during this time period, such as " If I Could Write a Book" in January 1952, which Granata sees as a "turning point", forecasting his later work with its sensitivity, Columbia and MCA dropped him later that year. His last studio recording for Columbia, "Why Try To Change Me Now", was recorded in New York on September 17, 1952, with an orchestra arranged and conducted by
Percy Faith Percy Faith (April 7, 1908 – February 9, 1976) was a Canadian–American bandleader, orchestrator, composer and conductor, known for his lush arrangements of instrumental ballads and Christmas standards. He is often credited with popularizin ...
. Journalist Burt Boyar observed, "Sinatra had had it. It was sad. From the top to the bottom in one horrible lesson."


1953–1960: Career revival and the Capitol years

The release of the film ''
From Here to Eternity ''From Here to Eternity'' is a 1953 American romantic Drama (film and television)#War drama, war drama film directed by Fred Zinnemann and written by Daniel Taradash, based on the 1951 From Here to Eternity (novel), novel of the same name by J ...
'' in August 1953 marked the beginning of a remarkable career revival. Tom Santopietro notes that Sinatra began to bury himself in his work, with an "unparalleled frenetic schedule of recordings, movies and concerts", in what authors Anthony Summers and Robbyn Swan describe as "a new and brilliant phase". On March 13, 1953, Sinatra met with Capitol Records vice president
Alan Livingston Alan Wendell Livingston (born Alan Wendell Levison; October 15, 1917 – March 13, 2009) was an American businessman best known for his tenures at Capitol Records, first as a writer/producer best known for creating Bozo the Clown for a series ...
and signed a seven-year recording contract. His first session for Capitol took place at KHJ studios at Studio C, 5515 Melrose Avenue in Los Angeles, with Axel Stordahl conducting. The session produced four recordings, including "
I'm Walking Behind You "I'm Walking Behind You" is a popular song which was written by Billy Reid and published in 1953. The recording by American singer Eddie Fisher was a No. 1 hit in both the US and UK Singles charts, but it had previously been recorded by Reid's ...
", Sinatra's first Capitol single. After spending two weeks on location in Hawaii filming ''From Here to Eternity'', Sinatra returned to KHJ on April 30 for his first recording session with
Nelson Riddle Nelson Smock Riddle Jr. (June 1, 1921 – October 6, 1985) was an American arranger, composer, bandleader and orchestrator whose career stretched from the late 1940s to the mid-1980s. He worked with many vocalists at Capitol Records, including ...
, an established arranger and conductor at Capitol who was Nat King Cole's musical director. After recording the first song, "
I've Got the World on a String "I've Got the World on a String" is a 1932 popular jazz song composed by Harold Arlen, with lyrics written by Ted Koehler. It was written for the twenty-first edition of the Cotton Club series which opened on October 23, 1932, the first of the C ...
", Sinatra offered Riddle a rare expression of praise, "Beautiful!", and after listening to the playbacks, he could not hide his enthusiasm, exclaiming, "I'm back, baby, I'm back!" In subsequent sessions in May and November 1953, Sinatra and Riddle developed and refined their musical collaboration, with Sinatra providing specific guidance on the arrangements. Sinatra's first album for Capitol, '' Songs for Young Lovers'', was released on January 4, 1954, and included "
A Foggy Day "A Foggy Day" is a popular song composed by George Gershwin, with lyrics by Ira Gershwin. The song was introduced by Fred Astaire in the 1937 film '' A Damsel in Distress''. It was originally titled "A Foggy Day (In London Town)" in reference to ...
", "
I Get a Kick Out of You "I Get a Kick Out of You" is a song by Cole Porter, which was first sung in the 1934 Broadway musical '' Anything Goes'', and then in the 1936 film version. Originally sung by Ethel Merman, it has been covered by dozens of prominent performers, ...
", "
My Funny Valentine "My Funny Valentine" is a show tune from the 1937 Rodgers and Hart coming of age musical ''Babes in Arms'' in which it was introduced by teenaged star Mitzi Green. The song became a popular jazz standard, appearing on over 1300 albums performed ...
", " Violets for Your Furs", and " They Can't Take That Away from Me", songs which became staples of his later concerts. That same month, Sinatra released the single " Young at Heart", which reached No. 2 and was awarded Song of the Year. In March, he recorded and released the single " Three Coins in the Fountain", a "powerful ballad" that reached No. 4. Sinatra's second album with Riddle, '' Swing Easy!'', which reflected his "love for the jazz idiom" according to Granata, was released on August 2 of that year and included " Just One of Those Things", "
Taking a Chance on Love "Taking a Chance on Love" is a popular song from the 1940 Broadway musical '' Cabin in the Sky''. It was introduced by Ethel Waters playing the role of Petunia Jackson both on Broadway and later in the 1943 MGM musical Cabin in the Sky. The so ...
", " Get Happy", and " All of Me". ''Swing Easy!'' was named Album of the Year by ''Billboard'', and he was named "Favorite Male Vocalist" by ''Billboard'', ''DownBeat'', and ''
Metronome A metronome () is a device that produces an audible click or other sound at a uniform interval that can be set by the user, typically in beats per minute (BPM). Metronomes may also include synchronized visual motion, such as a swinging pendulum ...
'' that year. Sinatra came to consider Riddle "the greatest arranger in the world", and Riddle, who considered Sinatra, "a perfectionist", said: "It's not only that his intuitions as to tempo, phrasing, and even configuration are amazingly right, but his taste is so impeccable... There is still no one who can approach him." Sinatra became one of Las Vegas's pioneer
residency Residency may refer to: * Artist-in-residence, a program to sponsor the residence and work of visual artists, writers, musicians, etc. * Concert residency, a series of concerts performed at one venue * Domicile (law), the act of establishing or m ...
entertainers, and a prominent figure on the Vegas scene throughout the 1950s and 1960s onwards, a period described by Rojek as the "high-water mark" of Sinatra's "hedonism and self-absorption". Rojek notes that the
Rat Pack The Rat Pack was an informal group of singers that, in its second iteration, ultimately made films and appeared together in Las Vegas casino venues. They originated in the late 1940s and early 1950s as a group of A-list show business friends, s ...
"provided an outlet for gregarious banter and wisecracks" but argues that it was Sinatra's vehicle, possessing an "unassailable command over the other performers". Sinatra would fly to Las Vegas from Los Angeles in Van Heusen's plane. On October 4, 1953, Sinatra made his first performance at the
Sands Hotel and Casino The Sands Hotel and Casino was a historic hotel and casino on the Las Vegas Strip in Paradise, Nevada, United States, that operated from 1952 to 1996. Designed by architect Wayne McAllister, with a prominent high sign, the Sands was the seve ...
, after an invitation by the manager
Jack Entratter Jack Entratter (February 28, 1914 – March 11, 1971), nicknamed "Mr. Entertainment", was an American business executive. He is best known for management positions at the Copacabana (nightclub), Copacabana nightclub in New York City in the 1940s ...
. Sinatra typically performed there three times a year and later acquired a share in the hotel. In 1955, Sinatra released ''
In the Wee Small Hours ''In the Wee Small Hours'' is the ninth studio album by American singer Frank Sinatra, released on April 25, 1955, by Capitol Records. Produced by Voyle Gilmore with arrangements by Nelson Riddle, the album's songs deal with themes such as i ...
'', his first 12" LP, featuring songs such as "
In the Wee Small Hours of the Morning "In the Wee Small Hours of the Morning" is a 1955 popular music, popular song composed by David Mann (songwriter), David Mann, with lyrics by Bob Hilliard. It was introduced as the title track of Frank Sinatra's 1955 album ''In the Wee Small Hou ...
", "
Mood Indigo "Mood Indigo" is a jazz song with music by Duke Ellington and Barney Bigard and lyrics by Irving Mills. Composition Although Irving Mills—Jack Mills's brother and publishing partner—took credit for the lyrics, Mitchell Parish claimed in a ...
", "
Glad to Be Unhappy "Glad to Be Unhappy" is a popular song composed by Rodgers and Hart. It was introduced in their 1936 musical ''On Your Toes'', sung by Doris Carson and David Morris, although it was not popular at the time, as there was only one recording of the ...
" and "
When Your Lover Has Gone "When Your Lover Has Gone" is a 1931 composition by Einar Aaron Swan which, after being featured in the James Cagney film '' Blonde Crazy'' that same year, has become a jazz standard Jazz standards are musical compositions that are an importa ...
". According to Granata it was the first
concept album A concept album is an album whose tracks hold a larger purpose or meaning collectively than they do individually. This is typically achieved through a single central narrative or theme, which can be instrumental, compositional, or lyrical. Som ...
of his to make a "single persuasive statement", with an extended program and "melancholy mood". Sinatra embarked on his first tour of Australia the same year. Another collaboration with Riddle resulted in '' Songs for Swingin' Lovers!'', sometimes seen as one of his best albums, which was released in March 1956. It features a recording of "
I've Got You Under My Skin "I've Got You Under My Skin" is a song written by American composer Cole Porter in 1936. It was introduced that year in the Eleanor Powell musical film ''Born to Dance'' in which it was performed by Virginia Bruce. It was nominated for the Aca ...
" by
Cole Porter Cole Albert Porter (June 9, 1891 – October 15, 1964) was an American composer and songwriter. Many of his songs became Standard (music), standards noted for their witty, urbane lyrics, and many of his scores found success on Broadway the ...
, which reportedly took 22 takes to perfect. His February 1956 recording sessions inaugurated the studios at the
Capitol Records Building The Capitol Records Building, also known as the Capitol Records Tower, is a 13-story tower building in the Hollywood neighborhood of Los Angeles, California, United States. Designed by Louis Naidorf of Welton Becket Associates, it is one of t ...
, complete with a 56-piece symphonic orchestra. According to Granata, his recordings of "Night and Day", "Oh! Look at Me Now", and " From This Moment On" revealed "powerful sexual overtones, stunningly achieved through the mounting tension and release of Sinatra's best-teasing vocal lines", while his recording of "River, Stay 'Way from My Door" in April demonstrated his "brilliance as a syncopational improviser". Riddle said that Sinatra took "particular delight" in singing "The Lady is a Tramp", commenting that he "always sang that song with a certain amount of salaciousness", making "cue tricks" with the lyrics. His penchant for conducting was displayed again in 1956's '' Frank Sinatra Conducts Tone Poems of Color'', an instrumental album that has been interpreted to be a catharsis to his failed relationship with Gardner. Sinatra also sang at that year's Democratic National Convention and performed with The Dorsey Brothers for a week soon afterward at the Paramount Theatre. In 1957, Sinatra released '' Close to You'', ''
A Swingin' Affair! ''A Swingin' Affair!'' is the twelfth studio album by Frank Sinatra. It is sometimes mentioned as the sequel to ''Songs for Swingin' Lovers''. "The Lady Is a Tramp" was bumped from the original album and replaced with "No One Ever Tells You" ...
'', and '' Where Are You?''—his first album in stereo, with
Gordon Jenkins Gordon Hill Jenkins (May 12, 1910 – May 1, 1984) was an American arranger, composer, and pianist who was influential in popular music in the 1940s and 1950s. Jenkins worked with The Andrews Sisters, Johnny Cash, The Weavers, Frank Sinatra, Lo ...
. Granata considers "Close to You" to have been thematically his closest concept album to perfection during the "golden" era, and Nelson Riddle's finest work, which was "extremely progressive" by the standards of the day. It is structured like a three-act play, each commencing with the songs " With Every Breath I Take", "
Blame It on My Youth "Blame It on My Youth" is a jazz standard written by Oscar Levant (music) and Edward Heyman (lyrics) in 1934. Recorded versions *1934: The Dorsey Brothers Orchestra (vocal by Bob Crosby) - recorded for Decca Records (catalog 320) on November ...
" and " It Could Happen to You". For Granata, Sinatra's ''A Swingin' Affair!'' and ''Songs for Swingin' Lovers!'' solidified "Sinatra's image as a 'swinger', from both a musical and visual standpoint."
Buddy Collette William Marcel "Buddy" Collette (August 6, 1921 – September 19, 2010) was an American jazz flutist, saxophonist, and clarinetist. He was a founding member of the Chico Hamilton Quintet. Early life William Marcel Collette was born in ...
considered the swing albums to have been heavily influenced by
Sammy Davis Jr. Samuel George Davis Jr. (December 8, 1925 – May 16, 1990) was an American singer, actor, comedian, dancer, and musician. At age two, Davis began his career in Vaudeville with his father Sammy Davis Sr. and the Will Mastin Trio, which t ...
and stated that when he worked with Sinatra in the mid-1960s, he approached a song much differently than he had done in the early 1950s. On June 9, 1957, he performed in a 62-minute concert conducted by Riddle at the Seattle Civic Auditorium, his first appearance in
Seattle Seattle ( ) is the most populous city in the U.S. state of Washington and in the Pacific Northwest region of North America. With a population of 780,995 in 2024, it is the 18th-most populous city in the United States. The city is the cou ...
since 1945.''Sinatra '57 in Concert'' (1999), Artanis Entertainment Group. The recording was first released as a bootleg, but Artanis Entertainment Group officially released it as '' Sinatra '57 in Concert'' in 1999, after Sinatra's death. In 1958, Sinatra released the concept album '' Come Fly with Me'' with
Billy May Edward William May Jr. (November 10, 1916 – January 22, 2004) was an American composer, arranger and trumpeter. He composed film and television music for ''The Green Hornet (TV series), The Green Hornet'' (1966), ''The Mod Squad (TV series), T ...
, designed as a musical world tour. It reached the top spot on the ''Billboard'' album chart in its second week, remaining at the top for five weeks, and was nominated for the
Grammy Award for Album of the Year The Grammy Award for Album of the Year is an award presented by the The Recording Academy, National Academy of Recording Arts and Sciences of the United States to "honor artistic achievement, technical proficiency and overall excellence in the r ...
at the inaugural Grammy Awards. The title song, " Come Fly With Me", written especially for him, would become one of his best-known standards. On May 29, he recorded seven songs in a single session, more than double the usual yield of a recording session, and an eighth, " Lush Life", was abandoned as Sinatra found it too technically demanding. In September, Sinatra released ''
Frank Sinatra Sings for Only the Lonely ''Frank Sinatra Sings for Only the Lonely'' (also known as ''Sings for Only the Lonely'' or simply ''Only the Lonely'') is the fifteenth studio album by American singer Frank Sinatra. It was released on September 8, 1958, through Capitol Records. ...
'', a stark collection of introspective saloon songs and blues-tinged ballads, which proved a huge commercial success, spending 120 weeks on ''Billboard''s album chart and peaking at No. 1. Cuts from this LP, such as " Angel Eyes" and "
One for My Baby (and One More for the Road) "One for My Baby (and One More for the Road)" is a song written by Harold Arlen and Johnny Mercer for the movie musical '' The Sky's the Limit'' (1943) and first performed in the film by Fred Astaire. Background Harold Arlen described the song ...
", would remain staples of the "saloon song" segments of Sinatra's concerts. In 1959, Sinatra released '' Come Dance with Me!'', a highly successful, critically acclaimed album that stayed on ''Billboard''s Pop album chart for 140 weeks, peaking at No. 2. It won the Grammy Award for Album of the Year, as well as Best Vocal Performance, Male and Best Arrangement for Billy May. He released '' No One Cares'' in the same year, a collection of "brooding, lonely" torch songs, which critic
Stephen Thomas Erlewine Stephen Thomas Erlewine (; born June 18, 1973) is an American music critic and former senior editor for the online music database AllMusic. He is the author of multiple artist biographies and record reviews for AllMusic, as well as a freelance ...
thought was "nearly as good as its predecessor ''Where Are You?'', but lacked the "lush" arrangements of it and the "grandiose melancholy" of ''Only the Lonely''. In the words of Kelley, by 1959, Sinatra was "not simply the leader of the Rat Pack" but had "assumed the position of ''il padrone'' in Hollywood." He was asked by 20th Century Fox to be the master of ceremonies at a luncheon attended by Soviet Premier
Nikita Khrushchev Nikita Sergeyevich Khrushchev (– 11 September 1971) was the General Secretary of the Communist Party of the Soviet Union, First Secretary of the Communist Party of the Soviet Union from 1953 to 1964 and the Premier of the Soviet Union, Chai ...
on September 19, 1959. ''
Nice 'n' Easy ''Nice 'n' Easy'' is the eighteenth studio album by Frank Sinatra, released on July 25, 1960. All the songs, with the notable exception of the title song, are sung as ballads and were arranged and conducted by Nelson Riddle. The title song was ...
'', a collection of ballads, topped the ''Billboard'' chart in October 1960 and remained in the charts for 86 weeks, winning critical plaudits.


1960–1969: Reprise years

Sinatra grew discontented at Capitol and feuded with
Alan Livingston Alan Wendell Livingston (born Alan Wendell Levison; October 15, 1917 – March 13, 2009) was an American businessman best known for his tenures at Capitol Records, first as a writer/producer best known for creating Bozo the Clown for a series ...
, which lasted over six months. His first attempt at owning his own label was with his pursuit of buying declining jazz label
Verve Records Verve Records is an active American record label owned by Universal Music Group (UMG). Founded in 1956 by Norman Granz, the label is home to the world's largest jazz catalogue, which includes recordings by artists such as Ella Fitzgerald, Ca ...
, which ended once an initial agreement with Verve founder
Norman Granz Norman Granz (August 6, 1918 – November 22, 2001) was an American jazz record producer and concert promoter. He founded the record labels Clef, Norgran, Down Home, Verve, and Pablo and the Jazz at the Philharmonic concert series. Gra ...
"failed to materialize". He decided to form his own label,
Reprise Records Reprise Records is an American record label founded in 1960 by Frank Sinatra. It is owned by Warner Music Group, and operates through Warner Records, one of its flagship labels. Artists currently signed to Reprise Records include Green Day, En ...
, and, in an effort to assert his new direction, temporarily parted with Riddle, May and Jenkins, working with other arrangers such as Neil Hefti,
Don Costa Dominick P. "Don" Costa (June 10, 1925 – January 19, 1983) was an American conductor and record producer. He discovered singer Paul Anka and worked on several hit albums by Frank Sinatra, including '' Sinatra and Strings'' and '' My Way'' ...
, and
Quincy Jones Quincy Delight Jones Jr. (March 14, 1933 – November 3, 2024) was an American record producer, composer, arranger, conductor, trumpeter, and bandleader. Over the course of his seven-decade career, he received List of awards and nominations re ...
. Sinatra built the appeal of Reprise Records as one in which artists were promised creative control, as well as a guarantee that they would eventually gain "complete ownership of their work, including publishing rights." Under Sinatra the company developed into a music industry "powerhouse", and he later sold it for an estimated $80million. His first album on the label, ''
Ring-a-Ding-Ding! ''Ring-a-Ding-Ding!'' is the twentieth studio album by Frank Sinatra, released on May 7, 1961. It was the inaugural record on Sinatra's Reprise label and, as the initial concept was "an album without ballads", it consisted only of uptempo swi ...
'' (1961), was a major success, peaking at No.4 on ''Billboard''. The album was released in February 1961, the same month that Reprise Records released
Ben Webster Benjamin Francis Webster (March 27, 1909 – September 20, 1973) was an American jazz tenor Saxophone, saxophonist. He performed in the United States and Europe and made many recordings with Duke Ellington, Billie Holiday, Johnny Hodges, a ...
's '' The Warm Moods'',
Sammy Davis Jr. Samuel George Davis Jr. (December 8, 1925 – May 16, 1990) was an American singer, actor, comedian, dancer, and musician. At age two, Davis began his career in Vaudeville with his father Sammy Davis Sr. and the Will Mastin Trio, which t ...
's ''The Wham of Sam'', Mavis River's ''Mavis'' and Joe E. Lewis's ''It is Now Post Time''. During the initial years of Reprise, Sinatra was still under contract to record for Capitol, completing his contractual commitment with the release of ''
Point of No Return The point of no return (PNR or PONR) is the point beyond which one must continue on one's current course of action because turning back is no longer possible, being too dangerous, physically difficult, or prohibitively expensive to be undertaken. ...
'', recorded on September 11 and 12, 1961. In 1962, Sinatra released '' Sinatra and Strings'', a set of standard ballads arranged by Don Costa, which became one of the most critically acclaimed works of Sinatra's Reprise period. Frank Jr., who was present during the recording, noted the "huge orchestra", which Nancy Sinatra stated "opened a whole new era" in pop music, with orchestras getting bigger, embracing a "lush string sound". Sinatra and
Count Basie William James "Count" Basie (; August 21, 1904 – April 26, 1984) was an American jazz pianist, organist, bandleader, and composer. In 1935, he formed the Count Basie Orchestra, and in 1936 took them to Chicago for a long engagement and the ...
collaborated for the album '' Sinatra-Basie'' the same year, a popular and successful release which prompted them to rejoin two years later for the follow-up '' It Might as Well Be Swing'', arranged by Quincy Jones. The two became frequent performers together, and appeared at the
Newport Jazz Festival The Newport Jazz Festival is an annual American multi-day jazz music festival held every summer in Newport, Rhode Island. Elaine Lorillard established the festival in 1954, and she and husband Louis Lorillard financed it for many years. They hire ...
in 1965. Also in 1962, as the owner of his own record label, Sinatra was able to step on the podium as conductor again, releasing his third instrumental album '' Frank Sinatra Conducts Music from Pictures and Plays''. In 1963, Sinatra reunited with Nelson Riddle for '' The Concert Sinatra'', an ambitious album featuring a 73-piece symphony orchestra arranged and conducted by Riddle. The concert was recorded on a motion picture scoring soundstage with the use of multiple synchronized recording machines that employed an optical signal onto 35mm film designed for movie soundtracks. Granata considers the album to have been "impeachable" ic "one of the very best of the Sinatra-Riddle ballad albums", in which Sinatra displayed his vocal range, particularly in "
Ol' Man River "Ol' Man River" is a show tune from the 1927 musical '' Show Boat'' with music by Jerome Kern and lyrics by Oscar Hammerstein II, who wrote the song in 1925. The song contrasts the struggles and hardships of African Americans with the endless, ...
", in which he darkened the hue. In 1964, the song "
My Kind of Town "My Kind of Town" or "My Kind of Town (Chicago Is)" is a popular song composed by Jimmy Van Heusen, with lyrics by Sammy Cahn. The song was originally part of the musical score for ''Robin and the 7 Hoods'', a 1964 musical film starring sever ...
" was nominated for the
Academy Award for Best Original Song The Academy Award for Best Original Song is one of the awards given annually to people working in the Film industry, motion picture industry by the Academy of Motion Picture Arts and Sciences (AMPAS). It is presented to the ''songwriters'' who h ...
. Sinatra released '' Softly, as I Leave You'', and collaborated with Bing Crosby and
Fred Waring Fredrick Malcolm Waring Sr. (June 9, 1900 – July 29, 1984) was an American musician, bandleader, choral director, and radio and television personality, sometimes referred to as "America's Singing Master" and "The Man Who Taught America How to ...
on '' America, I Hear You Singing'', a collection of patriotic songs recorded as a tribute to the assassinated President John F. Kennedy. Sinatra increasingly became involved in charitable pursuits in this period. In 1961 and 1962, he went to Mexico to put on performances for Mexican charities. and in July 1964, he was present at the dedication of the Frank Sinatra International Youth Center for Arab and Jewish children in
Nazareth Nazareth is the largest Cities in Israel, city in the Northern District (Israel), Northern District of Israel. In its population was . Known as "the Arab capital of Israel", Nazareth serves as a cultural, political, religious, economic and ...
. Sinatra's phenomenal success in 1965, coinciding with his 50th birthday, prompted ''Billboard'' to proclaim that he may have reached the "peak of his eminence". In June 1965, Sinatra, Sammy Davis Jr., and
Dean Martin Dean Martin (born Dino Paul Crocetti; June 7, 1917 – December 25, 1995) was an American singer, actor, and comedian. Nicknamed the "Honorific nicknames in popular music, King of Cool", he is regarded as one of the most popular entertainers of ...
played live in
St. Louis St. Louis ( , sometimes referred to as St. Louis City, Saint Louis or STL) is an independent city in the U.S. state of Missouri. It lies near the confluence of the Mississippi and the Missouri rivers. In 2020, the city proper had a populatio ...
to benefit Dismas House, a prisoner rehabilitation and training center with nationwide programs that, in particular, helped serve black Americans. The Rat Pack concert, called The Frank Sinatra Spectacular, was broadcast live via satellite to numerous movie theaters across America. The album '' September of My Years'' was released September 1965, and went on to win the Grammy Award for best album of the year. Granata considers the album to have been one of the finest of his Reprise years, "a reflective throwback to the concept records of the 1950s, and more than any of those collections, distills everything that Frank Sinatra had ever learned or experienced as a vocalist". One of the album's singles, " It Was a Very Good Year", won the Grammy Award for Best Vocal Performance, Male. A career anthology, '' A Man and His Music'', followed in November, winning Album of the Year at the Grammys the following year. In 1966, Sinatra released '' That's Life'', with both the single of " That's Life" and album becoming Top Ten hits on ''Billboard''s pop charts. ''
Strangers in the Night "Strangers in the Night" is a song composed by Bert Kaempfert with English lyrics by Charles Singleton and Eddie Snyder. Kaempfert originally used it under the title "Beddy Bye" as part of the instrumental score for the movie ''A Man Could Get ...
'' went on to top the ''Billboard'' and UK pop singles charts, winning the award for Record of the Year at the Grammys. Sinatra's first live album, '' Sinatra at the Sands'', was recorded during January and February 1966 at the Sands Hotel and Casino in Las Vegas. Sinatra was backed by the Count Basie Orchestra, with Quincy Jones conducting. Sinatra pulled out from the Sands the following year when he was driven out by its new owner
Howard Hughes Howard Robard Hughes Jr. (December 24, 1905 – April 5, 1976) was an American Aerospace engineering, aerospace engineer, business magnate, film producer, and investor. He was The World's Billionaires, one of the richest and most influential peo ...
after a fight. Sinatra started 1967 with a series of recording sessions with
Antônio Carlos Jobim Antônio Carlos Brasileiro de Almeida Jobim (25 January 1927 – 8 December 1994), also known as Tom Jobim (), was a Brazilian composer, pianist, guitarist, songwriter, arranger, and singer. Considered as one of the great exponents of Brazilian ...
. He recorded one of his collaborations with Jobim, the Grammy-nominated album ''
Francis Albert Sinatra & Antônio Carlos Jobim ''Francis Albert Sinatra & Antonio Carlos Jobim'' is a 1967 album by Frank Sinatra and Antônio Carlos Jobim. The tracks were arranged and conducted by Claus Ogerman, accompanied by a studio orchestra. Along with Jobim's original compositions, th ...
'', which was one of the best-selling albums of the year, behind the Beatles's ''
Sgt. Pepper's Lonely Hearts Club Band ''Sgt. Pepper's Lonely Hearts Club Band'' (often referred to simply as ''Sgt. Pepper'') is the eighth studio album by the English rock band the Beatles. Released on 26May 1967, ''Sgt. Pepper'' is regarded by musicologists as an early concept ...
''. According to Santopietro the album "consists of an extraordinarily effective blend of bossa nova and slightly swinging jazz vocals, and succeeds in creating an unbroken mood of romance and regret." Writer
Stan Cornyn Carl Stanley Cornyn (July 8, 1933 – May 11, 2015) was an American record label executive. He wrote ''Exploding: The Highs, Hits, Hype, Heroes, and Hustlers of the Warner Music Group'' (), and authored three privately published family genealogy ...
wrote that Sinatra sang so softly on the album that it was comparable to the time that he suffered from a vocal hemorrhage in 1950. Sinatra released the album ''
The World We Knew ''The World We Knew'', also known as ''Frank Sinatra'', is a 1967 studio album by American singer Frank Sinatra. The album's title track reached No. 30 on the US ''Billboard'' Hot 100 chart and #1 on the Easy Listening chart in 1967. Its second ...
'', which features a chart-topping duet of "
Somethin' Stupid "Somethin' Stupid", or "Something Stupid", is a song written by C. Carson Parks. It was originally recorded in 1966 by Parks and his wife Gaile Foote, as Carson and Gaile. A 1967 version by Frank Sinatra and his daughter Nancy Sinatra became ...
" with daughter Nancy. In December, Sinatra collaborated with
Duke Ellington Edward Kennedy "Duke" Ellington (April 29, 1899 – May 24, 1974) was an American Jazz piano, jazz pianist, composer, and leader of his eponymous Big band, jazz orchestra from 1924 through the rest of his life. Born and raised in Washington, D ...
on the album '' Francis A. & Edward K.''. According to Granata, the recording of "
Indian Summer An Indian summer is a period of unseasonably warm, dry weather that sometimes occurs in autumn in temperate regions of the northern hemisphere. Several sources describe a true Indian summer as not occurring until after the first frost, or mor ...
" on the album was a favorite of Riddle's, noting the "contemplative mood
hich Ij () is a village in Golabar Rural District of the Central District in Ijrud County, Zanjan province, Iran Iran, officially the Islamic Republic of Iran (IRI) and also known as Persia, is a country in West Asia. It borders Iraq ...
is heightened by a
Johnny Hodges Johnny Hodges (July 25, 1907 – May 11, 1970) was an American alto saxophone, alto saxophonist, best known for solo work with Duke Ellington's big band. He played lead alto in the saxophone section for many years. Hodges was also featured on sop ...
alto sax solo that will bring a tear to your eye". With Sinatra in mind, singer-songwriter
Paul Anka Paul Albert Anka (born July 30, 1941) is a Canadian and American singer, songwriter and actor. His songs include " Diana", “ You Are My Destiny", “Lonely Boy", " Put Your Head on My Shoulder", and " (You're) Having My Baby". Anka also wr ...
wrote the song "
My Way "My Way" is Paul Anka's English-language lyrical adaptation of the French song " Comme d'habitude", released by Frank Sinatra in 1969. The original song was written by Jacques Revaux, Gilles Thibaut, and Claude François, and was first recor ...
", using the melody of the French "Comme d'habitude" ("As Usual"), composed by
Claude François Claude Antoine Marie François (; 1 February 1939 – 11 March 1978), also known by the nickname Cloclo, was a French pop singer, composer, songwriter, record producer, drummer and dancer. François co-wrote the lyrics of " Comme d'habitude" ( ...
and
Jacques Revaux Jacques Abel Jules Revaud (; born 11 July 1940), known as Jacques Revaux (), is a French songwriter, most famous for his 1968 writing collaboration with singer Claude François on the song "", whose text was reworked by Canadian singer-songwriter ...
. Sinatra recorded it in one take, just after Christmas 1968. "My Way", Sinatra's best-known song on the Reprise label, was not an instant success, charting at No. 27 in the US and No. 5 in the UK. However, it remained in the UK charts for 122 weeks, including 75 non-consecutive weeks in the
Top 40 In the music industry, the Top 40 is a list of the 40 currently most popular songs in a particular genre. It is the best-selling or most frequently broadcast popular music. Record charts have traditionally consisted of a total of 40 songs. "To ...
, between April 1969 and September 1971, which was still a record in 2015. Sinatra told songwriter
Ervin Drake Ervin Drake (born Ervin Maurice Druckman; April 3, 1919 – January 15, 2015) was an American songwriter whose works include such American Songbook standards as " I Believe" and " It Was a Very Good Year". He wrote in a variety of styles and his ...
in the 1970s that he "detested" singing the song because he believed audiences would think it was a "self-aggrandizing tribute". According to
NPR National Public Radio (NPR) is an American public broadcasting organization headquartered in Washington, D.C., with its NPR West headquarters in Culver City, California. It serves as a national Radio syndication, syndicator to a network of more ...
, "My Way" has become one of the most requested songs at funerals. In an effort to maintain his commercial viability in the late 1960s, Sinatra would record works by
Paul Simon Paul Frederic Simon (born October 13, 1941) is an American singer-songwriter known for his solo work and his collaborations with Art Garfunkel. He and Garfunkel, whom he met in elementary school in 1953, came to prominence in the 1960s as Sim ...
("
Mrs. Robinson "Mrs. Robinson" is a song by American folk rock duo Simon & Garfunkel from their fourth Album, studio album, ''Bookends (album), Bookends'' (1968). The writing of the song was begun before the 1967 film ''The Graduate'', which contained only f ...
"),
the Beatles The Beatles were an English Rock music, rock band formed in Liverpool in 1960. The core lineup of the band comprised John Lennon, Paul McCartney, George Harrison and Ringo Starr. They are widely regarded as the Cultural impact of the Beatle ...
(" Yesterday"), and
Joni Mitchell Roberta Joan Mitchell (née Anderson; born November 7, 1943) is a Canadian and American singer-songwriter, multi-instrumentalist, and painter. As one of the most influential singer-songwriters to emerge from the 1960s folk music circuit, Mitch ...
("
Both Sides, Now "Both Sides, Now" is a song by Canadian singer-songwriter Joni Mitchell. One of the first recordings is by Judy Collins, whose version appeared on the US singles chart during the fall of 1968. (The earliest commercial release was by Dave Van Ro ...
") in 1969.


1970–1981: "Retirement" and return

In 1970, Sinatra released '' Watertown'', a critically acclaimed concept album, with music by
Bob Gaudio Robert John Gaudio (born November 17, 1942) is an American songwriter, singer, musician, and record producer, and the keyboardist and backing vocalist of the pop/rock band the Four Seasons. Gaudio wrote or co-wrote the vast majority of the ban ...
(of the Four Seasons) and lyrics by
Jake Holmes Jake Holmes (born December 28, 1939) is an American singer-songwriter and jingle writer who began a recording career in the 1960s. Holmes is the author of the song " Dazed and Confused", later reworked by Led Zeppelin. Holmes also composed the ...
. However, it sold a mere 30,000 copies that year and reached a peak chart position of 101. He left Caesars Palace in September of that year after an incident in which executive Sanford Waterman pulled a gun on him. He performed several charity concerts with Count Basie at the
Royal Festival Hall The Royal Festival Hall is a 2,700-seat concert, dance and talks venue within Southbank Centre in London, England. It is situated on the South Bank of the River Thames, not far from Hungerford Bridge, in the London Borough of Lambeth. It is a G ...
in London. On November 2, 1970, Sinatra recorded the last songs for Reprise Records before his self-imposed retirement, announced the following June at a concert in Hollywood to raise money for the Motion Picture and TV Relief Fund. He gave a "rousing" performance of "That's Life", and finished the concert with a
Matt Dennis Matthew Loveland Dennis (February 11, 1914 – June 21, 2002) was an American singer, pianist, band leader, arranger, and writer of music for popular songs. Biography Dennis was born in Seattle, Washington, United States. His mother was a viol ...
and Earl Brent song, "Angel Eyes" which he had recorded on the ''Only the Lonely'' album in 1958. He sang the last line. "'Scuse me while I disappear." The spotlight went dark, and he left the stage. He told ''LIFE'' journalist Thomas Thompson that "I've got things to do, like the first thing is not to do at all for eight months... maybe a year", while Barbara Sinatra later said that Sinatra had grown "tired of entertaining people, especially when all they really wanted were the same old tunes he had long ago become bored by". Around this time, Sinatra designed ''Villa Maggio'', a holiday home and retreat near Palm Desert. While he was in retirement, President
Richard Nixon Richard Milhous Nixon (January 9, 1913April 22, 1994) was the 37th president of the United States, serving from 1969 until Resignation of Richard Nixon, his resignation in 1974. A member of the Republican Party (United States), Republican ...
asked him to perform at a Young Voters Rally in anticipation of the upcoming campaign. Sinatra obliged and chose to sing "My Kind of Town" for the rally held in Chicago on October 20, 1972. In 1973, Sinatra came out of his short-lived retirement with a television special and album. The album, entitled ''
Ol' Blue Eyes Is Back ''Ol' Blue Eyes Is Back'' is a 1973 studio album by American singer Frank Sinatra. Sinatra returned from his brief retirement with ''Ol' Blue Eyes Is Back''. Released amidst a whirlwind of publicity, the album was a commercial success, earnin ...
'', arranged by Gordon Jenkins and
Don Costa Dominick P. "Don" Costa (June 10, 1925 – January 19, 1983) was an American conductor and record producer. He discovered singer Paul Anka and worked on several hit albums by Frank Sinatra, including '' Sinatra and Strings'' and '' My Way'' ...
, was a success, reaching number 13 on ''Billboard'' and number 12 in the UK. The television special, ''
Magnavox Presents Frank Sinatra ''Magnavox Presents Frank Sinatra'' (or ''Ol' Blue Eyes Is Back'') is an NBC musical television special starring Frank Sinatra broadcast on November 18, 1973. The special was written by Fred Ebb, directed by Marty Pasetta, and produced by Howard ...
'', reunited Sinatra with
Gene Kelly Eugene Curran Kelly (August 23, 1912 – February 2, 1996) was an American dancer, actor, singer, director and choreographer. He was known for his energetic and athletic dancing style and sought to create a new form of American dance accessibl ...
. He initially developed problems with his vocal cords during the comeback due to a prolonged period without singing. That Christmas, he performed at the
Sahara Hotel Sahara Las Vegas is a hotel and casino located on the Las Vegas Strip in Winchester, Nevada. It is owned and operated by the Meruelo Group. The hotel has 1,616 rooms, and the casino contains . The Sahara anchors the northern end of the Las Veg ...
in Las Vegas, and returned to Caesars Palace the following month in January 1974. He began what Barbara Sinatra describes as a "massive comeback tour of the United States, Europe, the Far East, and Australia." In July, while on a second tour of Australia, he caused an uproar by describing journalists therewho were aggressively pursuing his every move and pushing for a press conferenceas "bums, parasites, fags, broads and buck-and-a-half hookers." After he was pressured to apologize, Sinatra instead insisted that the journalists apologize for "fifteen years of abuse I have taken from the world press." Union actions canceled concerts and grounded Sinatra's plane, essentially trapping him in Australia. Sinatra's lawyer, Mickey Rudin, arranged for Sinatra to issue a written conciliatory note and a final concert that was televised to the nation. In October 1974, he appeared at New York City's
Madison Square Garden Madison Square Garden, colloquially known as the Garden or by its initials MSG, is a multi-purpose indoor arena in New York City. It is located in Midtown Manhattan between Seventh Avenue (Manhattan), Seventh and Eighth Avenue (Manhattan), Eig ...
in a televised concert that was later released as an album under the title '' The Main Event – Live''. Backing him was bandleader
Woody Herman Woodrow Charles Herman (May 16, 1913 – October 29, 1987) was an American jazz Jazz is a music genre that originated in the African-American communities of New Orleans, Louisiana, in the late 19th and early 20th centuries. Its roo ...
and the Young Thundering Herd, who accompanied Sinatra on a European tour later that month. In 1975, Sinatra performed in concerts in New York with Count Basie and
Ella Fitzgerald Ella Jane Fitzgerald (April25, 1917June15, 1996) was an American singer, songwriter and composer, sometimes referred to as the "First Lady of Song", "Queen of Jazz", and "Lady Ella". She was noted for her purity of tone, impeccable diction, phra ...
, and at the
London Palladium The London Palladium () is a Grade II* West End theatre located on Argyll Street, London, in Soho. The theatre was designed by Frank Matcham and opened in 1910. The auditorium holds 2,286 people. Hundreds of stars have played there, many wit ...
with Basie and
Sarah Vaughan Sarah Lois Vaughan (, March 27, 1924 – April 3, 1990) was an American jazz singer and pianist. Nicknamed "Sassy" and "List of nicknames of jazz musicians, The Divine One", she won two Grammy Awards, including the Lifetime Achievement Award, ...
, and in Tehran at Aryamehr Stadium, giving 140 performances in 105 days. In August he held several concerts at
Lake Tahoe Lake Tahoe (; Washo language, Washo: ''dáʔaw'') is a Fresh water, freshwater lake in the Sierra Nevada of the Western United States, straddling the border between California and Nevada. Lying at above sea level, Lake Tahoe is the largest a ...
together with the newly risen singer
John Denver Henry John Deutschendorf Jr. (December 31, 1943 – October 12, 1997), known professionally as John Denver, was an American Country music, country and Folk music, folk singer, songwriter, and actor. He was one of the most popular acoustic m ...
, who became a frequent collaborator. Sinatra had recorded Denver's "
Leaving on a Jet Plane "Leaving on a Jet Plane" is a song written and recorded by American singer John Denver in 1966, originally included on his debut demo recording ''John Denver Sings''. Its original title was "Babe I Hate to Go". He made several copies and gave t ...
" and " My Sweet Lady" for '' Sinatra & Company'' (1971), and according to Denver, his song "A Baby Just Like You" was written at Sinatra's request for his new grandchild, Angela. During the Labor Day weekend held in 1976, Sinatra was responsible for reuniting old friends and comedy partners Dean Martin and
Jerry Lewis Jerry Lewis (born Joseph Levitch; March 16, 1926 – August 20, 2017) was an American comedian, actor, singer, filmmaker and humanitarian, with a career spanning seven decades in film, stage, television and radio. Famously nicknamed as "Th ...
for the first time in nearly twenty years, when they performed at the "
Jerry Lewis MDA Telethon The ''MDA Labor Day Telethon'' was an annual telethon held on (starting the night before and throughout) Labor Day in the United States to raise money for the Muscular Dystrophy Association (MDA). The Muscular Dystrophy Association was founded i ...
". That year, the Friars Club selected him as the "Top Box Office Name of the Century", and he was given the Scopus Award by the American Friends of the
Hebrew University of Jerusalem The Hebrew University of Jerusalem (HUJI; ) is an Israeli public university, public research university based in Jerusalem. Co-founded by Albert Einstein and Chaim Weizmann in July 1918, the public university officially opened on 1 April 1925. ...
in Israel and an honorary Doctor of Humane Letters from the
University of Nevada The University of Nevada, Reno (Nevada, the University of Nevada, or UNR) is a public land-grant research university in Reno, Nevada, United States. It is the state's flagship public university and primary land grant institution. It was founded ...
. Sinatra continued to perform at Caesars Palace in the late 1970s and was performing there in January 1977 when his mother Dolly died in a plane crash on the way to see him. He canceled two weeks of shows and spent time recovering from the shock in Barbados. In March, he performed in front of
Princess Margaret Princess Margaret, Countess of Snowdon (Margaret Rose; 21 August 1930 – 9 February 2002) was the younger daughter of King George VI and Queen Elizabeth The Queen Mother. She was the younger sister and only sibling of Queen Elizabeth II. ...
at the
Royal Albert Hall The Royal Albert Hall is a concert hall on the northern edge of South Kensington, London, England. It has a seating capacity of 5,272. Since the hall's opening by Queen Victoria in 1871, the world's leading artists from many performance genres ...
in London, raising money for the
National Society for the Prevention of Cruelty to Children The National Society for the Prevention of Cruelty to Children (NSPCC) is a British child protection charity founded as the Liverpool Society for the Prevention of Cruelty to Children (LSPCC) by Thomas Agnew on 19 April 1883. The NSPCC lobbies t ...
. On March 14, he recorded with Nelson Riddle for the last time, recording the songs "
Linda Linda is an English feminine given name, derived from the Spanish word , meaning "pretty." Linda may also refer to: Names * Linda (given name), a female given name (including a list of people and fictional characters so named) * Linda (singer) ...
", "Sweet Lorraine", and "Barbara". The two men had a major falling out and later patched up their differences in January 1985 at a dinner organized for Ronald Reagan when Sinatra asked Riddle to make another album with him. Riddle was ill at the time and died that October before they had a chance to record. In 1978, Sinatra filed a $1million lawsuit against a land developer for using his name in the "Frank Sinatra Drive Center" in West Los Angeles. During a party at Caesars in 1979, he was awarded the Grammy Trustees Award, while celebrating 40 years in show business and his 64th birthday. That year, former President
Gerald Ford Gerald Rudolph Ford Jr. (born Leslie Lynch King Jr.; July 14, 1913December 26, 2006) was the 38th president of the United States, serving from 1974 to 1977. A member of the Republican Party (United States), Republican Party, Ford assumed the p ...
awarded Sinatra the International Man of the Year Award, and he performed in front of the
Egyptian pyramids The Egyptian pyramids are ancient masonry structures located in Egypt. Most were built as tombs for the pharaohs and their consorts during the Old Kingdom of Egypt, Old and Middle Kingdom of Egypt, Middle Kingdom periods. At least 138 identi ...
for
Anwar Sadat Muhammad Anwar es-Sadat (25 December 1918 – 6 October 1981) was an Egyptian politician and military officer who served as the third president of Egypt, from 15 October 1970 until Assassination of Anwar Sadat, his assassination by fundame ...
, which raised more than $500,000 for Sadat's wife's charities. In 1980, Sinatra's first album in six years was released, '' Trilogy: Past Present Future'', a highly ambitious triple album that features an array of songs from both the pre-rock and rock eras. It was the first studio album of Sinatra's to feature his touring pianist at the time, Vinnie Falcone, and was based on an idea by
Sonny Burke Joseph Francis "Sonny" Burke (March 22, 1914 – May 31, 1980) was an American musical arranger, composer, Big Band leader and producer. Early life and career Born in Scranton, Pennsylvania to Francis P. Burke and Rhoda Nihany, Burke grew up in D ...
. The album garnered six
Grammy The Grammy Awards, stylized as GRAMMY, and often referred to as The Grammys, are awards presented by The Recording Academy of the United States to recognize outstanding achievements in music. They are regarded by many as the most prestigious a ...
nominations– winning for best liner notes– and peaked at number 17 on ''Billboard''s album chart, and spawned yet another song that would become a signature tune, "
Theme from New York, New York "Theme from ''New York, New York''", often abbreviated to just "New York, New York", is the theme song from the Martin Scorsese musical film ''New York, New York'' (1977), composed by John Kander, with lyrics by Fred Ebb. Liza Minnelli perfo ...
". That year, as part of the Concert of the Americas, he performed in the
Maracanã Stadium Maracanã Stadium (, ; named after the Maracanã River), officially known as Jornalista Mário Filho Stadium (, ; , named after Mário Filho), is an association football stadium in Rio de Janeiro, Brazil. Located in the Maracanã neighbor ...
in
Rio de Janeiro Rio de Janeiro, or simply Rio, is the capital of the Rio de Janeiro (state), state of Rio de Janeiro. It is the List of cities in Brazil by population, second-most-populous city in Brazil (after São Paulo) and the Largest cities in the America ...
, Brazil, which broke records for the "largest live paid audience ever recorded for a solo performer". The following year, Sinatra built on the success of ''Trilogy'' with '' She Shot Me Down'', an album that was praised for embodying the dark tone of his Capitol years." ''She Shot Me Down'' AllMusic. Retrieved November 28, 2006. Also in 1981, Sinatra was embroiled in controversy when he worked a 10-day engagement for $2million in Sun City, in the internationally unrecognized
Bophuthatswana Bophuthatswana (, ), officially the Republic of Bophuthatswana (; ), and colloquially referred to as the Bop and by outsiders as Jigsawland (In reference to its enclave-ridden borders) was a Bantustan (also known as "Homeland", an area set asid ...
, breaking a cultural boycott against apartheid-era South Africa. President
Lucas Mangope Kgosi Lucas Manyane Mangope (27 December 1923 – 18 January 2018) was the leader of the Bantustan (homeland) of Bophuthatswana. The territory he ruled over was distributed between the Orange Free State – what is now Free State – and North ...
awarded Sinatra with the highest honor, the Order of the Leopard, and made him an honorary tribal chief.


1982–1995: Later career and final projects

Santopietro stated that by the early 1980s, Sinatra's voice had "coarsened, losing much of its power and flexibility, but audiences didn't care." In 1982, he signed a $16million three-year deal with the Golden Nugget of Las Vegas. Kelley notes that by this period, Sinatra's voice had grown "darker, tougher and loamier", but he "continued to captivate audiences with his immutable magic." She added that his baritone voice "sometimes cracked, but the gliding intonations still aroused the same raptures of delight as they had at the Paramount Theater." That year, he made a reported further $1.3million from the Showtime television rights to his "Concert of the Americas" in the Dominican Republic, $1.6million for a concert series at
Carnegie Hall Carnegie Hall ( ) is a concert venue in Midtown Manhattan, New York City. It is at 881 Seventh Avenue (Manhattan), Seventh Avenue, occupying the east side of Seventh Avenue between 56th Street (Manhattan), 56th and 57th Street (Manhattan), 57t ...
, and $250,000 in just one evening at the Chicago Fest. He donated a lot of his earnings to charity. He put on a performance at the White House for Italian president
Sandro Pertini Alessandro Giuseppe Antonio "Sandro" Pertini (; 25 September 1896 – 24 February 1990) was an Italian socialist politician and statesman who served as President of Italy from 1978 to 1985. Early life Born in Stella (province of Savona) as t ...
, and performed at the
Radio City Music Hall Radio City Music Hall (also known as Radio City) is an entertainment venue and Theater (structure), theater at 1260 Sixth Avenue (Manhattan), Avenue of the Americas, within Rockefeller Center, in the Midtown Manhattan neighborhood of New York C ...
with
Luciano Pavarotti Luciano Pavarotti (, , ; 12 October 19356 September 2007) was an Italian operatic tenor who during the late part of his career crossed over into popular music, eventually becoming one of the most acclaimed tenors of all time. He made numerou ...
and
George Shearing Sir George Albert Shearing (13 August 191914 February 2011) was a British jazz pianist who for many years led a popular jazz group that recorded for Discovery Records, MGM Records and Capitol Records. Shearing was the composer of over 300 so ...
. Sinatra was honored at the 1983
Kennedy Center Honors The Kennedy Center Honors are annual honors given to those in the performing arts for their lifetime of contributions to Culture of the United States, American culture. They have been presented annually since 1978, culminating each December in ...
, alongside
Katherine Dunham Katherine Mary Dunham (June 22, 1909 – May 21, 2006) was an African American dancer, choreographer, anthropologist, and social activist. Dunham had one of the most successful dance careers of the 20th century and directed her own dance compan ...
,
James Stewart James Maitland Stewart (May 20, 1908 – July 2, 1997) was an American actor and military aviator. Known for his distinctive drawl and everyman screen persona, Stewart's film career spanned 80 films from 1935 to 1991. With the strong morali ...
,
Elia Kazan Elias Kazantzoglou (, ; September 7, 1909 – September 28, 2003), known as Elia Kazan ( ), was a Greek-American film and theatre director, producer, screenwriter and actor, described by ''The New York Times'' as "one of the most honored and inf ...
, and
Virgil Thomson Virgil Thomson (November 25, 1896 – September 30, 1989) was an American composer and critic. He was instrumental in the development of the "American Sound" in classical music. He has been described as a modernist, a neoromantic, a neoclassic ...
. Quoting
Henry James Henry James ( – ) was an American-British author. He is regarded as a key transitional figure between literary realism and literary modernism, and is considered by many to be among the greatest novelists in the English language. He was the ...
, President Reagan said in honoring his old friend that "art was the shadow of humanity" and that Sinatra had "spent his life casting a magnificent and powerful shadow." On September 21, 1983, Sinatra filed a $2million court case against
Kitty Kelley Katherine Kelley (born April 4, 1942) is an American journalist and author of best-selling unauthorized biographies of Jacqueline Kennedy Onassis, Elizabeth Taylor, Frank Sinatra, Nancy Reagan, the British royal family, the Bush family, and O ...
, suing her for punitive damages, before her unofficial biography, ''His Way'', was even published. The book became a best-seller for "all the wrong reasons" and "the most eye-opening celebrity biography of our time", according to
William Safire William Lewis Safire (; Safir; December 17, 1929 – September 27, 2009Safire, William (1986). ''Take My Word for It: More on Language.'' Times Books. . p. 185.) was an American author, columnist, journalist, and presidential speechwriter. He ...
of ''The New York Times''. Sinatra was always adamant that such a book would be written on his terms, and he himself would "set the record straight" in details of his life. According to Kelley, the family detested her and the book, which took its toll on Sinatra's health. Kelley says that Tina Sinatra blamed her for her father's colon surgery in 1986. He was forced to drop the case on September 19, 1984, with several leading newspapers expressing concerns about censorship. In 1984, Sinatra worked with Quincy Jones for the first time in nearly two decades on the album '' L.A. Is My Lady'', which was well received critically. The album was a substitute for another Jones project, an album of duets with
Lena Horne Lena Mary Calhoun Horne (June 30, 1917 – May 9, 2010) was an American singer, actress, dancer and civil rights activist. Horne's career spanned more than seventy years and covered film, television and theatre. Horne joined the chorus of the C ...
, which had to be abandoned. In 1986, Sinatra collapsed on stage while performing in
Atlantic City Atlantic City, sometimes referred to by its initials A.C., is a Jersey Shore seaside resort city in Atlantic County, in the U.S. state of New Jersey. Atlantic City comprises the second half of the Atlantic City- Hammonton metropolitan sta ...
and was hospitalized for
diverticulitis Diverticulitis, also called colonic diverticulitis, is a gastrointestinal disease characterized by inflammation of abnormal pouches—Diverticulum, diverticula—that can develop in the wall of the large intestine. Symptoms typically include lo ...
, which left him looking frail. Two years later, Sinatra reunited with Martin and Davis and went on the Rat Pack Reunion Tour, during which they played many large arenas. When Martin dropped out of the tour early on, a rift developed between them, and the two never spoke again. On June 6, 1988, Sinatra made his last recordings with Reprise for an album that was not released. He recorded " My Foolish Heart", " Cry Me a River", and other songs. Sinatra never completed the project, but take number 18 of "My Foolish Heart" may be heard in '' The Complete Reprise Studio Recordings'' (1995). In 1990, Sinatra was awarded the second "Ella Award" by the Los Angeles-based
Society of Singers Society of Singers, (1984 – 2017), known as SOS, was an American nonprofit 501(c)3 charitable organization, the only one devoted exclusively to helping professional singers. History and programs SOS was co-founded in 1984 by Ginny Mancini, wido ...
, and performed for a final time with Ella Fitzgerald at the award ceremony. Sinatra maintained an active touring schedule in the early 1990s, performing 65 concerts in 1990, 73 in 1991, and 84 in 1992 in seventeen countries. In 1993, Sinatra returned to Capitol Records and the recording studio for '' Duets'', which became his best-selling album. The album and its sequel, '' Duets II'', released the following year, would see Sinatra remake his classic recordings with popular contemporary performers, who added their vocals to a pre-recorded tape. During his tours in the early 1990s, his memory failed him at times during concerts, and he fainted onstage in
Richmond, Virginia Richmond ( ) is the List of capitals in the United States, capital city of the Commonwealth (U.S. state), U.S. commonwealth of Virginia. Incorporated in 1742, Richmond has been an independent city (United States), independent city since 1871. ...
in March 1994. His final public concerts were held in
Fukuoka Dome , officially the is a domed baseball field located in Chūō-ku, Fukuoka, Japan. Home to the Fukuoka SoftBank Hawks, the 40,000 seat stadium was built in 1993 and was originally named Fukuoka Dome. It is Japan's first stadium built with a retra ...
in Japan on December 19–20, 1994. The following year, Sinatra sang for the last time on February 25, 1995, before a live audience of 1200 select guests at the Palm Desert Marriott Ballroom on the closing night of the Frank Sinatra Desert Classic golf tournament. ''
Esquire Esquire (, ; abbreviated Esq.) is usually a courtesy title. In the United Kingdom, ''esquire'' historically was a title of respect accorded to men of higher social rank, particularly members of the landed gentry above the rank of gentleman ...
'' reported of the show that Sinatra was "clear, tough, on the money" and "in absolute control". Sinatra was awarded the Legend Award at the
1994 Grammy Awards The 36th Annual Grammy Awards were held on March 1, 1994. They recognized accomplishments by musicians from the previous year. Whitney Houston was the Big Winner winning 3 awards including Record of the Year and Album of the Year while opening ...
, where he was introduced by
Bono Paul David Hewson (born 10 May 1960), known by the nickname Bono ( ), is an Irish singer-songwriter and activist. He is a founding member, the lead vocalist, and primary lyricist of the rock band U2. Bono is known for his impassioned voca ...
, who said of him, "Frank's the chairman of the bad attitude... Rock 'n roll plays at being tough, but this guy is the boss– the chairman of boss". In 1995, to mark Sinatra's 80th birthday, the
Empire State Building The Empire State Building is a 102-story, Art Deco-style supertall skyscraper in the Midtown South neighborhood of Manhattan, New York City, United States. The building was designed by Shreve, Lamb & Harmon and built from 1930 to 1931. Its n ...
glowed blue. A star-studded birthday tribute, ''Sinatra: 80 Years My Way'', was held at the
Shrine Auditorium The Shrine Auditorium is a landmark large-event venue in Los Angeles, California. It is also the headquarters of the Al Malaikah Temple, a division of the Shriners. It was designated a Los Angeles Historic-Cultural Monument (No. 139) in 1975, an ...
in Los Angeles, featuring performers such as
Ray Charles Ray Charles Robinson (September 23, 1930 – June 10, 2004) was an American singer, songwriter, and pianist. He is regarded as one of the most iconic and influential musicians in history, and was often referred to by contemporaries as "The Gen ...
,
Little Richard Richard Wayne Penniman (December 5, 1932 – May 9, 2020), known professionally as Little Richard, was an American singer, pianist, and songwriter. He was an influential figure in popular music and culture for seven decades. Described as the "Ar ...
,
Natalie Cole Natalie Maria Cole (February 6, 1950 – December 31, 2015) was an American singer, songwriter, and actress. She was the daughter of singer and jazz pianist Nat King Cole. She rose to prominence in the mid-1970s, with the release of her debut ...
and
Salt-N-Pepa Salt-N-Pepa (sometimes stylized as Salt 'N' Pepa) is an American hip-hop, hip hop group formed in New York City in 1985, that comprised Salt (rapper), Salt (Cheryl James), Pepa (rapper), Pepa (Sandra Denton), and DJ Spinderella (Deidra Roper). ...
singing his songs. At the end of the program, Sinatra performed on stage for the last time to sing the final notes of the "Theme from New York, New York" with an ensemble. In recognition of his many years of association with Las Vegas, Sinatra was elected to the Gaming Hall of Fame in 1997.


Artistry

While Sinatra never learned how to read music well, he had a natural understanding of it, and he worked very hard from a young age to improve his abilities in all aspects of music. He could follow a
lead sheet A lead sheet or fake sheet is a form of musical notation that specifies the essential elements of a popular song: the melody, lyrics and harmony. The melody is written in modern Western music notation, the lyric is written as text below the s ...
(simplified sheet music showing a song's basic structure) during a performance by "carefully following the patterns and groupings of notes arranged on the page" and made his own notations to the music, using his ear to detect semitonal differences. Granata states that some of the most accomplished classically trained musicians soon noticed his musical understanding and remarked that Sinatra had a "sixth sense", which "demonstrated unusual proficiency when it came to detecting incorrect notes and sounds within the orchestra." Sinatra was an aficionado of classical music, and would often request classical strains in his music, inspired by composers such as
Puccini Giacomo Puccini (22 December 1858 29 November 1924) was an Italian composer known primarily for his operas. Regarded as the greatest and most successful proponent of Italian opera after Verdi, he was descended from a long line of composers, s ...
and
Impressionist Impressionism was a 19th-century art movement characterized by visible brush strokes, open Composition (visual arts), composition, emphasis on accurate depiction of light in its changing qualities (often accentuating the effects of the passage ...
masters. His personal favorite was
Ralph Vaughan Williams Ralph Vaughan Williams ( ; 12 October 1872– 26 August 1958) was an English composer. His works include operas, ballets, chamber music, secular and religious vocal pieces and orchestral compositions including nine symphonies, written over ...
. He would insist on always recording live with the band because it gave him a "certain feeling" to perform live surrounded by musicians. By the mid-1940s, such was his understanding of music that after hearing an air check of some compositions by
Alec Wilder Alexander Lafayette Chew Wilder (February 16, 1907 – December 24, 1980) was an American composer and author. Biography Wilder was born in Rochester, New York, United States, to a prominent family; the Wilder Building downtown (at the "Four ...
, which were for strings and woodwinds, he became the conductor at Columbia Records for six of Wilder's compositions. The works were considered by Wilder to have been among the finest renditions and recordings of his compositions, past or present. Critic Gene Lees, a lyricist and the author of the words to the Jobim melody "This Happy Madness", expressed amazement when he heard Sinatra's recording of it on '' Sinatra & Company'' (1971), considering him to have delivered the lyrics to perfection. Voice coach John Quinlan was impressed by Sinatra's vocal range, remarking, "He has far more voice than people think he has. He can vocalize to a B-flat on top in full voice, and he doesn't need a mic either". As a singer, early on, he was primarily influenced by Bing Crosby, but later believed that
Tony Bennett Anthony Dominick Benedetto (August 3, 1926 – July 21, 2023), known professionally as Tony Bennett, was an American jazz and traditional pop singer. He received many accolades, including 20 Grammy Awards, a Grammy Lifetime Achievement Award, ...
was "the best singer in the business." Bennett himself claimed that as a performer, Sinatra had "perfected the art of intimacy." According to Nelson Riddle, Sinatra had a "fairly rangy voice", remarking that "His voice has a very strident, insistent sound in the top register, a smooth lyrical sound in the middle register, and a very tender sound in the low. His voice is built on infinite taste, with an overall inflection of sex. He points everything he does from a sexual standpoint". Despite his heavy New Jersey accent, when Sinatra sang, his accent was barely detectable; according to Richard Schuller, his diction became "precise" while singing and his articulation "meticulous". His timing was impeccable, allowing him, according to Charles L. Granata, to "toy with the rhythm of a melody, bringing tremendous excitement to his reading of a lyric." Tommy Dorsey observed that Sinatra would "take a musical phrase and play it all the way through seemingly without breathing for eight, ten, maybe sixteen bars." Dorsey was a considerable influence on Sinatra's techniques for his vocal phrasing with his own exceptional breath control on the trombone, and Sinatra regularly swam and held his breath underwater, thinking of song lyrics to increase his breathing power. Arrangers such as Nelson Riddle and Anthony Fanzo found Sinatra to be a perfectionist who constantly drove himself and others around him, stating that his collaborators approached him with uneasiness because of his unpredictable and often volatile temperament. Granata comments that Sinatra was almost fanatically obsessed with perfection to the point that people began wondering if he was genuinely concerned about the music or showing off his power over others. On days when he felt that his voice was not right, he would know after only a few notes and would postpone the recording session until the following day, yet still pay his musicians. After a period of performing, Sinatra tired of singing a certain set of songs and was always looking for talented new songwriters and composers to work with. Once he found ones that he liked, he actively sought to work with them as often as he could and made friends with many of them. Over the years, he recorded 87 of
Sammy Cahn Samuel Cohen (June 18, 1913 – January 15, 1993), known professionally as Sammy Cahn, was an American lyricist, songwriter, and musician. He is best known for his romantic lyrics to films and Broadway songs, as well as stand-alone songs premie ...
's songs, of which 24 were composed by
Jule Styne Jule Styne ( ; born Julius Kerwin Stein; December 31, 1905 – September 20, 1994) was an English-American songwriter and composer widely known for a series of Broadway theatre, Broadway musical theatre, musicals, including several famous frequ ...
and 43 by Jimmy Van Heusen. The Cahn-Styne partnership lasted from 1942 until 1954, when Van Heusen succeeded him as Sinatra's main composer. Unlike many of his contemporaries, Sinatra insisted upon direct input regarding arrangements and tempos for his recordings. He would spend weeks thinking about the songs he wanted to record and would keep an arranger in mind for each song. Barbara Sinatra notes that Sinatra would almost always credit the songwriter at the end of each number and would often make comments to the audience, such as "Isn't that a pretty ballad" or "Don't you think that's the most marvelous love song", delivered with "childlike delight". She states that after each show, Sinatra would be "in a buoyant, electrically charged mood, a post-show high that would take him hours to come down from as he quietly relived every note of the performance he'd just given." Sinatra's split with Gardner in the fall of 1953 had a profound impact on the types of songs he sang and on his voice. He began to console himself in songs with a "brooding melancholy", such as "
I'm a Fool to Want You "I'm a Fool to Want You" is a 1951 song composed by Frank Sinatra, Jack Wolf, and Joel Herron. Frank Sinatra co-wrote the lyrics and released the song as a Columbia Records single. The Sentimental ballad, ballad is considered a popular music, po ...
", " Don't Worry 'Bout Me", "
My One and Only Love "My One and Only Love" is a 1953 popular song with music written by Guy Wood and lyrics by Robert Mellin.Gioia, T. (2012). ''The Jazz Standards: A Guide to the Repertoire''. Oxford University Press. . pp. 284-285. Notable renditions by Frank Si ...
" and "
There Will Never Be Another You "There Will Never Be Another You" is a popular song with music by Harry Warren and lyrics by Mack Gordon that was written for the Twentieth Century Fox musical ''Iceland'' (1942) starring Sonja Henie and John Payne. The songs in the film featur ...
", which Riddle believed was the direct influence of Ava Gardner. Lahr comments that the new Sinatra was "not the gentle boy balladeer of the forties. Fragility had gone from his voice, to be replaced by a virile adult's sense of happiness and hurt". Author Granata considered Sinatra a "master of the art of recording", noting that his work in the studio "set him apart from other gifted vocalists." During his career, he made over 1000 recordings. Recording sessions would typically last three hours. However, Sinatra would always prepare for them by spending at least an hour by the piano beforehand to vocalize, followed by a short rehearsal with the orchestra to ensure the balance of sound. During his Columbia years, Sinatra used an
RCA Type 44 The RCA Type 44 microphone is a bi-directional ribbon microphone, or pressure-gradient microphone, first introduced by the RCA Corporation in 1931. History Dr. Harry F. Olson began working for RCA Laboratories, where he developed ribbon micropho ...
microphone, which Granata describes as "the 'old-fashioned' microphone which is closely associated with Sinatra's crooner image of the 1940s". At Capitol, he used a
Neumann U 47 The Neumann is a large-diaphragm condenser microphone. It is one of the most famous studio microphones and was Neumann's first microphone after the Second World War. The original series, manufactured by Georg Neumann GmbH between 1949 and 1965 ...
, an "ultra-sensitive" microphone that better captured the timbre and tone of his voice. In the 1950s, Sinatra's career was facilitated by developments in technology. Up to sixteen songs could now be held by the twelve-inch L.P., and this allowed Sinatra to use song in a novelistic way, turning each track into a kind of chapter, which built and counterpointed moods to illuminate a larger theme". Santopietro writes that through the 1950s and well into the 1960s, "Every Sinatra LP was a masterpiece of one sort of another, whether uptempo, torch song, or swingin' affairs. Track after track, the brilliant concept albums redefined the nature of pop vocal art".


Film career


1941–1952: Debut, musical films, and career slump

Sinatra attempted to pursue an acting career in Hollywood in the early 1940s. While films appealed to him, being exceptionally self-confident, he was rarely enthusiastic about his own acting, once remarking that "pictures stink". Sinatra made his film debut performing in an uncredited sequence in '' Las Vegas Nights'' (1941), singing "I'll Never Smile Again" with Tommy Dorsey's Pied Pipers. He had a cameo role along with Duke Ellington and Count Basie in Charles Barton's '' Reveille with Beverly'' (1943), making a brief appearance singing " Night and Day". Next, he was given leading roles in '' Higher and Higher'' and '' Step Lively'' (both 1944) for
RKO RKO Radio Pictures Inc., commonly known as RKO Pictures or simply RKO, is an American film production and distribution company, historically one of the "Big Five" film studios of Hollywood's Golden Age. The business was formed after the Kei ...
.
Metro-Goldwyn-Mayer Metro-Goldwyn-Mayer Studios Inc. (also known as Metro-Goldwyn-Mayer Pictures, commonly shortened to MGM or MGM Studios) is an American Film production, film and television production and film distribution, distribution company headquartered ...
cast Sinatra opposite
Gene Kelly Eugene Curran Kelly (August 23, 1912 – February 2, 1996) was an American dancer, actor, singer, director and choreographer. He was known for his energetic and athletic dancing style and sought to create a new form of American dance accessibl ...
and
Kathryn Grayson Kathryn Grayson (born Zelma Kathryn Elisabeth Hedrick; February 9, 1922 – February 17, 2010) was an American actress and coloratura soprano. From the age of 12, Grayson trained as an opera singer. She was under contract to Metro-Goldwyn-Mayer ...
in the
Technicolor Technicolor is a family of Color motion picture film, color motion picture processes. The first version, Process 1, was introduced in 1916, and improved versions followed over several decades. Definitive Technicolor movies using three black-and ...
musical '' Anchors Aweigh'' (1945), in which he played a sailor on leave in Hollywood. A major success, it garnered several Academy Award wins and nominations, and the song "
I Fall in Love Too Easily "I Fall in Love Too Easily" is a 1944 song composed by Jule Styne with lyrics by Sammy Cahn. It was introduced by Frank Sinatra in the 1945 film '' Anchors Aweigh''. The film won an Academy Award for its music; "I Fall in Love Too Easily" was no ...
", sung by Sinatra in the film, was nominated for the
Academy Award for Best Original Song The Academy Award for Best Original Song is one of the awards given annually to people working in the Film industry, motion picture industry by the Academy of Motion Picture Arts and Sciences (AMPAS). It is presented to the ''songwriters'' who h ...
. He briefly appeared at the end of
Richard Whorf Richard Whorf (June 4, 1906 – December 14, 1966) was an American actor, writer and film director. Life and acting career Whorf was born in Winthrop, Massachusetts to Harry and Sarah (née Lee) Whorf. His older brother was linguist Benjamin ...
's commercially successful ''
Till the Clouds Roll By ''Till the Clouds Roll By'' is a 1946 American Technicolor musical film produced by Metro-Goldwyn-Mayer and a fictionalized biopic of composer Jerome Kern, portrayed by Robert Walker (actor, born 1918), Robert Walker. Kern was involved with the ...
'' (1946), a Technicolor musical biopic of
Jerome Kern Jerome David Kern (January 27, 1885 – November 11, 1945) was an American composer of musical theatre and popular music. One of the most important American theatre composers of the early 20th century, he wrote more than 700 songs, used in over ...
, in which he sang "
Ol' Man River "Ol' Man River" is a show tune from the 1927 musical '' Show Boat'' with music by Jerome Kern and lyrics by Oscar Hammerstein II, who wrote the song in 1925. The song contrasts the struggles and hardships of African Americans with the endless, ...
". Sinatra co-starred again with Gene Kelly in the Technicolor musical ''
Take Me Out to the Ball Game "Take Me Out to the Ball Game" is a 1908 waltz song by Jack Norworth and Albert Von Tilzer which has become the unofficial anthem of North American baseball, although neither of its authors had attended a game before writing the song. The song' ...
'' (1949), in which they play baseball players who are part-time vaudevillians. He teamed up with Kelly for a third time in '' On the Town'' (1949), playing a sailor on leave in New York City. The film remains rated very highly by critics, and in 2006, it ranked No. 19 on the
American Film Institute The American Film Institute (AFI) is an American nonprofit film organization that educates filmmakers and honors the heritage of the History of cinema in the United States, motion picture arts in the United States. AFI is supported by private fu ...
's list of best musicals. Both '' Double Dynamite'' (1951), an RKO
Irving Cummings Irving Cummings (October 9, 1888 – April 18, 1959) was an American movie actor and director. Career Born in New York City, Cummings started his acting career at age 16 in ''Diplomacy (play), Diplomacy''. His Broadway theatre, Broadway, p ...
comedy produced by
Howard Hughes Howard Robard Hughes Jr. (December 24, 1905 – April 5, 1976) was an American Aerospace engineering, aerospace engineer, business magnate, film producer, and investor. He was The World's Billionaires, one of the richest and most influential peo ...
, and
Joseph Pevney Joseph Pevney (September 15, 1911 – May 18, 2008) was an American film and television director. Biography Born in New York City, Pevney made his debut in vaudeville as a boy soprano in 1924. Although he hated vaudeville, he loved the thea ...
's '' Meet Danny Wilson'' (1952) failed to make an impression.


1953–1959: Career comeback and prime

Fred Zinnemann Alfred Zinnemann (April 29, 1907 – March 14, 1997) was an American film director and producer. He won four Academy Awards for directing and producing films in various genres, including thriller film, thrillers, western (genre), westerns, film ...
's ''
From Here to Eternity ''From Here to Eternity'' is a 1953 American romantic Drama (film and television)#War drama, war drama film directed by Fred Zinnemann and written by Daniel Taradash, based on the 1951 From Here to Eternity (novel), novel of the same name by J ...
'' (1953) deals with the tribulations of three soldiers, played by
Burt Lancaster Burton Stephen Lancaster (November 2, 1913 – October 20, 1994) was an American actor. Initially known for playing tough characters with tender hearts, he went on to achieve success with more complex and challenging roles over a 45-year caree ...
,
Montgomery Clift Edward Montgomery Clift (October 17, 1920 – July 23, 1966) was an American actor. A four-time Academy Award nominee, he was known for his portrayal of "moody, sensitive young men", according to ''The New York Times''. He is best remembered f ...
, and Sinatra, stationed on
Hawaii Hawaii ( ; ) is an island U.S. state, state of the United States, in the Pacific Ocean about southwest of the U.S. mainland. One of the two Non-contiguous United States, non-contiguous U.S. states (along with Alaska), it is the only sta ...
in the months leading up to the
attack on Pearl Harbor The attack on Pearl HarborAlso known as the Battle of Pearl Harbor was a surprise military strike by the Empire of Japan on the United States Pacific Fleet at Naval Station Pearl Harbor, its naval base at Pearl Harbor on Oahu, Territory of ...
. Sinatra had long been desperate to find a film role that would bring him back into the spotlight, and Columbia Pictures boss
Harry Cohn Harry Cohn (July 23, 1891 – February 27, 1958) was a co-founder, president, and production director of Columbia Pictures, Columbia Pictures Corporation. Life and career Cohn was born to a working-class Jewish family in New York City. His fath ...
had been inundated by appeals from people across Hollywood to give Sinatra a chance to star as "Maggio" in the film. During production, Montgomery Clift became a close friend, and Sinatra later professed that he "learned more about acting from him than anybody I ever knew before". After several years of critical and commercial decline, his
Academy Award for Best Supporting Actor The Academy Award for Best Supporting Actor is an award presented annually by the Academy of Motion Picture Arts and Sciences (AMPAS). It has been awarded since the 9th Academy Awards to an actor who has delivered an outstanding performance in ...
win helped him regain his position as the top recording artist in the world. His performance also won a
Golden Globe Award for Best Supporting Actor – Motion Picture The Golden Globe Award for Best Supporting Actor – Motion Picture is a Golden Globe Awards, Golden Globe Award that was first awarded by the Hollywood Foreign Press Association in 1944 for a performance in a motion picture released in the previ ...
. The ''Los Angeles Examiner'' wrote that Sinatra is "simply superb, comical, pitiful, childishly brave, pathetically defiant", commenting that his death scene is "one of the best ever photographed". Sinatra starred opposite
Doris Day Doris Day (born Doris Mary Kappelhoff; April 3, 1922 – May 13, 2019) was an American actress and singer. She began her career as a big band singer in 1937, achieving commercial success in 1945 with two No. 1 recordings, "Sentimental Journey ...
in the musical film '' Young at Heart'' (1954), and earned critical praise for his performance as a psychopathic killer posing as an
FBI The Federal Bureau of Investigation (FBI) is the domestic Intelligence agency, intelligence and Security agency, security service of the United States and Federal law enforcement in the United States, its principal federal law enforcement ag ...
agent opposite
Sterling Hayden Sterling Walter Hayden (born Sterling Relyea Walter; March 26, 1916 – May 23, 1986) was an American actor, author, sailor, and Marine. A leading man for most of his career, he specialized in Westerns and film noir throughout the 1950s, in film ...
in the
film noir Film noir (; ) is a style of Cinema of the United States, Hollywood Crime film, crime dramas that emphasizes cynicism (contemporary), cynical attitudes and motivations. The 1940s and 1950s are generally regarded as the "classic period" of Ameri ...
'' Suddenly'' (1954). Sinatra was nominated for an
Academy Award for Best Actor The Academy Award for Best Actor is an award presented annually by the Academy of Motion Picture Arts and Sciences (AMPAS). It has been awarded since the 1st Academy Awards to an actor who has delivered an outstanding performance in a leading ...
and
BAFTA Award for Best Actor in a Leading Role Best Actor in a Leading Role is a British Academy Film Awards, British Academy Film Award presented annually by the British Academy of Film and Television Arts (BAFTA) to recognise an actor who has delivered an outstanding leading performance in ...
for his role as a heroin addict in ''
The Man with the Golden Arm ''The Man with the Golden Arm'' is a 1955 American independent drama film noir directed by Otto Preminger, based on the novel of the same name by Nelson Algren. Starring Frank Sinatra, Eleanor Parker, Kim Novak, Arnold Stang and Darren Mc ...
'' (1955). After roles in ''
Guys and Dolls ''Guys and Dolls'' is a musical theater, musical with music and lyrics by Frank Loesser and book by Jo Swerling and Abe Burrows. It is based on "The Idyll of Miss Sarah Brown" (1933) and "Blood Pressure", which are two short stories by Damon Run ...
'', and '' The Tender Trap'' (both 1955), Sinatra was nominated for a BAFTA Award for Best Actor in a Leading Role for his role as a medical student in
Stanley Kramer Stanley Earl Kramer (September 29, 1913February 19, 2001) was an American film director and producer, responsible for making many of Hollywood's most famous " message films" (he called his movies ''heavy dramas'') and a liberal movie icon.
's directorial début, ''
Not as a Stranger ''Not as a Stranger'' is a 1955 American film noir drama film produced and directed by Stanley Kramer, starring Olivia de Havilland, Robert Mitchum, Frank Sinatra and Gloria Grahame. It is based on the 1954 novel of the same name by Morton Th ...
'' (1955). During production, Sinatra got drunk with
Robert Mitchum Robert Charles Durman Mitchum (August 6, 1917 – July 1, 1997) was an American actor. He is known for his antihero roles and film noir appearances. He received nominations for an Academy Award and a BAFTA Award. He received a star on the Holl ...
and
Broderick Crawford William Broderick Crawford (December 9, 1911 – April 26, 1986) was an American actor. He is best known for his portrayal of Willie Stark in the film ''All the King's Men'' (1949), which earned him an Academy Award and a Golden Globe Award. Of ...
and trashed Kramer's dressing room. Kramer vowed at the time never to hire Sinatra again and later regretted casting him as a Spanish guerrilla leader in ''
The Pride and the Passion ''The Pride and the Passion'' is a 1957 American Napoleonic-era war film in Technicolor and VistaVision from United Artists, produced and directed by Stanley Kramer, starring Cary Grant, Frank Sinatra, and Sophia Loren. The film co-stars ...
'' (1957). Sinatra featured alongside
Bing Crosby Harry Lillis "Bing" Crosby Jr. (May 3, 1903 – October 14, 1977) was an American singer, comedian, entertainer and actor. The first multimedia star, he was one of the most popular and influential musical artists of the 20th century worldwi ...
and
Grace Kelly Grace Patricia Kelly (November 12, 1929 – September 14, 1982), also known as Grace of Monaco, was an American actress and Princess of Monaco as the wife of Prince Rainier III from their marriage on April 18, 1956, until her death in 1982. ...
in ''
High Society High society, sometimes simply Society, is the behavior and lifestyle of people with the highest levels of wealth, power, fame and social status. It includes their related affiliations, social events and practices. Upscale social clubs were open ...
'' (1956) for MGM, earning a reported $250,000 for the picture. The public rushed to the cinemas to see Sinatra and Crosby together on-screen, and it ended up earning over $13million at the box office, becoming one of the highest-grossing pictures of its year. He starred opposite
Rita Hayworth Rita Hayworth (born Margarita Carmen Cansino; October 17, 1918May 14, 1987) was an American actress, dancer, and Pin-up model, pin-up girl. She achieved fame in the 1940s as one of the top stars of the Classical Hollywood cinema, Golden Age of ...
and
Kim Novak Marilyn Pauline "Kim" Novak (born February 13, 1933) is an American retired actress and painter. Her contributions to cinema have been honored with two Golden Globe Awards, an Honorary Golden Bear, a Golden Lion for Lifetime Achievement, and a s ...
in
George Sidney George Sidney (October 4, 1916May 5, 2002) was an American film director and producer who worked primarily at Metro-Goldwyn-Mayer. His work includes cult classics '' Bye Bye Birdie'' (1963) and '' Viva Las Vegas'' (1964). With an extensive back ...
's '' Pal Joey'' (1957), for which Sinatra won a
Golden Globe Award for Best Actor – Motion Picture Musical or Comedy Golden means made of, or relating to gold. Golden may also refer to: Places United Kingdom *Golden, in the parish of Probus, Cornwall *Golden Cap, Dorset *Golden Square, Soho, London *Golden Valley, a valley on the River Frome in Gloucestershir ...
. Santopietro considers the scene in which Sinatra sings "
The Lady Is a Tramp "The Lady Is a Tramp" is a show tune from the 1937 Rodgers and Hart musical '' Babes in Arms'', in which it was introduced by former child star Mitzi Green. This song is a spoof of New York high society and its strict etiquette (the first line ...
" to have been the finest moment of his film career. He next portrayed comedian Joe E. Lewis in ''
The Joker Is Wild ''The Joker Is Wild'' is a 1957 American musical drama film directed by Charles Vidor, starring Frank Sinatra, Mitzi Gaynor, Jeanne Crain and Eddie Albert, and released by Paramount Pictures. The VistaVision film is about Joe E. Lewis, the p ...
'' (1957); the song "
All the Way All the Way may refer to: Film and television * ''All the Way'' (1998 film), an Australian comedy directed by Marque Owen * ''All the Way'' (2001 film), a film directed by Shi Runjiu * ''All the Way'' (2016 film), an adaptation of Robert Schenk ...
" won the
Academy Award for Best Original Song The Academy Award for Best Original Song is one of the awards given annually to people working in the Film industry, motion picture industry by the Academy of Motion Picture Arts and Sciences (AMPAS). It is presented to the ''songwriters'' who h ...
. By 1958, Sinatra was one of the ten biggest box office draws in the United States, appearing with Dean Martin and
Shirley MacLaine Shirley MacLaine (born Shirley MacLean Beaty; April 24, 1934) is an American actress and author. With a career spanning over 70 years, she has received List of awards and nominations received by Shirley MacLaine, numerous accolades, including a ...
in
Vincente Minnelli Vincente Minnelli (; born Lester Anthony Minnelli; February 28, 1903 – July 25, 1986) was an American Theatre director, stage director and film director. From a career spanning over half a century, he is best known for his sophisticated innovat ...
's '' Some Came Running'' and '' Kings Go Forth'' (both 1958) with
Tony Curtis Tony Curtis (born Bernard Schwartz; June 3, 1925September 29, 2010) was an American actor with a career that spanned six decades, achieving the height of his popularity in the 1950s and early 1960s. He acted in more than 100 films, in roles co ...
and
Natalie Wood Natalie Wood (née Zacharenko; July 20, 1938 – November 29, 1981) was an American actress. She began acting at age four and co-starred at age eight in ''Miracle on 34th Street'' (1947). As a teenager, she was nominated for an Academy Award f ...
. " High Hopes", sung by Sinatra in the
Frank Capra Frank Russell Capra (born Francesco Rosario Capra; May 18, 1897 – September 3, 1991) was an Italian-American film director, producer, and screenwriter who was the creative force behind Frank Capra filmography#Films that won Academy Award ...
comedy, ''
A Hole in the Head ''A Hole in the Head'' is a 1959 DeLuxe Color CinemaScope American comedy film directed by Frank Capra and starring Frank Sinatra, Edward G. Robinson, Eleanor Parker, Keenan Wynn, Carolyn Jones and Thelma Ritter and released by United Artists.' ...
'' (1959), won the Academy Award for Best Original Song, and became a chart hit, lasting on the
Hot 100 The ''Billboard'' Hot 100, also known as simply the Hot 100, is the music industry standard record chart in the United States for songs, published weekly by ''Billboard'' magazine. Chart rankings are based on sales (physical and digital), o ...
for 17 weeks.


1960–1980: Later career

Due to an obligation, he owed to
20th Century Fox 20th Century Studios, Inc., formerly 20th Century Fox, is an American film studio, film production and Film distributor, distribution company owned by the Walt Disney Studios (division), Walt Disney Studios, the film studios division of the ...
for walking off the set of Henry King's ''
Carousel A carousel or carrousel (mainly North American English), merry-go-round (International English), or galloper (British English) is a type of amusement ride consisting of a rotating circular platform with seats for riders. The seats are tradit ...
'' (1956), Sinatra starred opposite
Shirley MacLaine Shirley MacLaine (born Shirley MacLean Beaty; April 24, 1934) is an American actress and author. With a career spanning over 70 years, she has received List of awards and nominations received by Shirley MacLaine, numerous accolades, including a ...
,
Maurice Chevalier Maurice Auguste Chevalier (; 12 September 1888 – 1 January 1972) was a French singer, actor, and entertainer. He is best known for his signature songs, including " Livin' In The Sunlight", " Valentine", " Louise", " Mimi", and " Thank Heaven f ...
and
Louis Jourdan Louis Jourdan (born Louis Robert Gendre; 19 June 1921 – 14 February 2015) was a French film and television actor. He was known for his suave roles in several Hollywood films, including Alfred Hitchcock's '' The Paradine Case'' (1947), '' Let ...
in ''
Can-Can The can-can (also spelled cancan as in the original French /kɑ̃kɑ̃/) is a high-energy, physically demanding dance that became a popular music-hall dance in the 1840s, continuing in popularity in French cabaret to this day. Originally dance ...
'' (1960). He earned $200,000 and 25% of the profits for the performance. Around the same time, he starred in the Las Vegas-set ''
Ocean's 11 ''Ocean's 11'' is a 1960 American heist film directed and produced by Lewis Milestone from a screenplay by Harry Brown and Charles Lederer, based on a story by George Clayton Johnson and Jack Golden Russell. The film stars an ensemble cast a ...
'' (1960), the first film to feature the Rat Pack together and the start of a "new era of screen cool" for Santopietro. Sinatra personally financed the film and paid Martin and Davis fees of $150,000 and $125,000, respectively, sums considered exorbitant for the period. He had a leading role opposite
Laurence Harvey Laurence Harvey (born Zvi Mosheh Skikne; 1 October 192825 November 1973) was a Lithuanian-born British actor and film director. He was born to Lithuanian Jewish parents and emigrated to Union of South Africa, South Africa at an early age, before ...
in ''
The Manchurian Candidate ''The Manchurian Candidate'' is a novel by Richard Condon, first published in 1959. It is a political thriller about the son of a prominent U.S. political family who is brainwashed into being an unwitting assassin for a communist conspiracy. T ...
'' (1962), which he considered to be the role he was most excited about and the high point of his film career.
Vincent Canby Vincent Canby (July 27, 1924 – October 15, 2000) was an American film and theatre critic who was the chief film critic for ''The New York Times'' from 1969 until the early 1990s, then its chief theatre critic from 1994 until his death in 2000. ...
, writing for the magazine ''Variety'', found the portrayal of Sinatra's character to be "a wide-awake pro creating a straight, quietly humorous character of some sensitivity." He appeared with the Rat Pack in the western ''
Sergeants 3 ''Sergeants 3'' is a 1962 American comedy/ Western film directed by John Sturges and starring Rat Pack icons Frank Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford and Joey Bishop. It was the last film to feature all five members o ...
'' (1962), and again in the 1964 gangster-oriented musical ''
Robin and the 7 Hoods ''Robin and the 7 Hoods'' is a 1964 American musical film directed by Gordon Douglas and starring Frank Sinatra, Dean Martin, Sammy Davis Jr. and Bing Crosby. It features Peter Falk and Barbara Rush, with an uncredited cameo by Edward G. Rob ...
''. For his performance in ''
Come Blow Your Horn ''Come Blow Your Horn'' is Neil Simon's first play, which premiered on Broadway in 1961 and had a London production in 1962 at the Prince of Wales Theatre. Simon rewrote the script more than two dozen times over several years, resulting in a hit ...
'' (1963), adapted from the
Neil Simon Marvin Neil Simon (July 4, 1927 – August 26, 2018) was an American playwright, screenwriter and author. He wrote more than 30 plays and nearly the same number of movie screenplays, mostly film adaptations of his plays. He received three ...
play, he was nominated for the
Golden Globe Award The Golden Globe Awards are awards presented for excellence in both international film and television. It is an annual award ceremony held since 1944 to honor artists and professionals and their work. The ceremony is normally held every Janua ...
for Best Actor– Motion Picture Musical or Comedy. Sinatra directed '' None but the Brave'' (1965), and ''
Von Ryan's Express ''Von Ryan's Express'' is a 1965 World War II adventure film starring Frank Sinatra, Trevor Howard, and Raffaella Carrà, and directed by Mark Robson. Produced in CinemaScope, the film depicts a group of Allied prisoners of war (POWs) who cond ...
'' (1965) was a major success. In the late 1960s, Sinatra became known for playing detectives, including Tony Rome in ''
Tony Rome ''Tony Rome'' is a 1967 American neo-noir mystery crime thriller film directed by Gordon Douglas and starring Frank Sinatra in the title role, alongside Jill St. John, Sue Lyon and Gena Rowlands. It was adapted from Marvin H. Albert's novel ...
'' (1967) and its sequel ''
Lady in Cement ''Lady in Cement'' is a 1968 American neo-noir mystery crime comedy thriller film directed by Gordon Douglas, based on the 1961 novel ''The Lady in Cement'' by Marvin H. Albert. The film stars Frank Sinatra, Raquel Welch, Dan Blocker, Richar ...
'' (1968). He played a similar role in '' The Detective'' (1968). As ''
Die Hard ''Die Hard'' is a 1988 American action film directed by John McTiernan and written by Jeb Stuart (writer), Jeb Stuart and Steven E. de Souza, based on the 1979 novel ''Nothing Lasts Forever (Thorp novel), Nothing Lasts Forever'' by Roderick ...
'' was based on the novel sequel to ''The Detective'', the studio was contractually obliged to offer Sinatra the role. Sinatra, who was 70 at the time, declined. Sinatra starred opposite
George Kennedy George Harris Kennedy Jr. (February 18, 1925 – February 28, 2016) was an American actor who appeared in more than 100 film and television productions. He played "Dragline" in ''Cool Hand Luke'' (1967), winning the Academy Award for Best Supp ...
in the western ''
Dirty Dingus Magee ''Dirty Dingus Magee'' is a 1970 American comedy revisionist Western film starring Frank Sinatra as the titular outlaw and George Kennedy as a sheriff out to capture him. Directed by Burt Kennedy, the movie was based on the novel ''The Ballad ...
'' (1970), an "abysmal" affair according to Santopietro, which was panned by the critics. The following year, Sinatra received a Golden Globe Cecil B. DeMille Award and had intended to play Detective Harry Callahan in ''
Dirty Harry ''Dirty Harry'' is a 1971 American action-thriller film produced and directed by Don Siegel, the first in the Dirty Harry (film series), ''Dirty Harry'' series. Clint Eastwood plays the title role, in his first appearance as San Francisco Polic ...
'' (1971), but had to turn down the role due to developing Dupuytren's contracture in his hand. Sinatra's last major film role was opposite
Faye Dunaway Dorothy Faye Dunaway (born January 14, 1941) is an American actress. She is the recipient of List of awards and nominations received by Faye Dunaway, many accolades, including an Academy Award, a Primetime Emmy Award, three Golden Globe Awards, ...
in Brian G. Hutton's '' The First Deadly Sin'' (1980). Santopietro said that as a troubled New York City homicide cop, Sinatra gave an "extraordinarily rich", heavily layered characterization, one which "made for one terrific farewell" to his film career.


Television and radio career

After beginning on the ''
Major Bowes Amateur Hour The ''Major Bowes Amateur Hour'' was an American radio talent show broadcast in the 1930s and 1940s, created and hosted by Edward Bowes (1874–1946). Selected performers from the program participated in touring vaudeville performances, under ...
'' radio show with the Hoboken Four in 1935, and later WNEW and WAAT in Jersey City, Sinatra became the star of radio shows of his own on
NBC The National Broadcasting Company (NBC) is an American commercial broadcast television and radio network serving as the flagship property of the NBC Entertainment division of NBCUniversal, a subsidiary of Comcast. It is one of NBCUniversal's ...
and
CBS CBS Broadcasting Inc., commonly shortened to CBS (an abbreviation of its original name, Columbia Broadcasting System), is an American commercial broadcast television and radio network serving as the flagship property of the CBS Entertainme ...
from the early 1940s to the mid-1950s. In 1942, Sinatra hired arranger Axel Stordahl away from Tommy Dorsey before he began his first radio program that year, keeping Stordahl with him for all of his radio work.. By the end of 1942, he was named the "Most Popular Male Vocalist on Radio" in a ''DownBeat'' poll. Early on he frequently worked with
The Andrews Sisters The Andrews Sisters were an American close harmony singing group of the swing and boogie-woogie eras. The group consisted of three sisters: contralto LaVerne Sophia Andrews (1911–1967), soprano Maxene Anglyn Andrews (1916–1995), and mezzo ...
on radio. They would appear as guests on each other's shows, as well as on many USO shows broadcast to troops via the
Armed Forces Radio Service The American Forces Network (AFN) is a government television and radio broadcast service the United States Armed Forces provides to soldiers stationed or assigned overseas, and is headquartered at Fort Meade in Maryland. AFN comprises two sub ...
(AFRS). He appeared as a special guest in the sisters' ABC ''Eight-to-the-Bar Ranch'' series, while the trio in turn guested on his '' Songs by Sinatra'' series on CBS. Sinatra had two stints as a regular member of the cast of ''
Your Hit Parade ''Your Hit Parade'' is an American radio and television music program that was broadcast from 1935 to 1953 on radio, and seen from 1950 to 1959 on television. It was sponsored by American Tobacco's Lucky Strike cigarettes. During its 24-year r ...
''; his first was from 1943 to 1945, and second was from 1946 to May 28, 1949, during which he was paired with the then-new girl singer,
Doris Day Doris Day (born Doris Mary Kappelhoff; April 3, 1922 – May 13, 2019) was an American actress and singer. She began her career as a big band singer in 1937, achieving commercial success in 1945 with two No. 1 recordings, "Sentimental Journey ...
. Starting in September 1949, the BBD&O advertising agency produced a radio series starring Sinatra for Lucky Strike called ''Light Up Time''– some 176 15-minute shows that featured him and
Dorothy Kirsten Dorothy Kirsten (July 6, 1910, Montclair, New Jersey – November 18, 1992, Los Angeles, California) was an American operatic soprano who was the first singer in the Metropolitan Opera's history to perform on that stage for 30 consecutive years, ...
singing– which lasted through to May 1950. In October 1951, the second season of '' The Frank Sinatra Show'' began on
CBS Television CBS Broadcasting Inc., commonly shortened to CBS (an abbreviation of its original name, Columbia Broadcasting System), is an American commercial broadcast television and radio network serving as the flagship property of the CBS Entertainme ...
. Ultimately, Sinatra did not find the success on television for which he had hoped. Santopietro writes that Sinatra "never appeared fully at ease on his own television series." In 1953 and 1954, Sinatra starred in the NBC radio program '' Rocky Fortune'', portraying Rocco Fortunato (a.k.a. Rocky Fortune). In 1957, Sinatra formed a three-year $3million contract with ABC to launch '' The Frank Sinatra Show'', featuring himself and guests in 36 half-hour shows. ABC agreed to allow Sinatra's Hobart Productions to keep 60% of the residuals and bought stock in Sinatra's film production unit, Kent Productions, guaranteeing him $7million. Though an initial critical success upon its debut on October 18, 1957, it soon attracted negative reviews from ''Variety'' and ''
The New Republic ''The New Republic'' (often abbreviated as ''TNR'') is an American magazine focused on domestic politics, news, culture, and the arts from a left-wing perspective. It publishes ten print magazines a year and a daily online platform. ''The New Y ...
'', and ''
The Chicago Sun-Times The ''Chicago Sun-Times'' is a daily Non-profit journalism, nonprofit newspaper published in Chicago, Illinois, United States. Since 2022, it is the flagship paper of Chicago Public Media, and has long held the second largest circulation am ...
'' thought that Sinatra and frequent guest Dean Martin "performed like a pair of adult delinquents", "sharing the same cigarette and leering at girls." In return, Sinatra later made numerous appearances on ''
The Dean Martin Show ''The Dean Martin Show'' is a TV Variety show, variety-Television comedy, comedy series that ran from 1965 to 1974 for 264 episodes. It was broadcast by NBC and hosted by Dean Martin. The theme song to the series was his 1964 hit "Everybody Loves ...
'' and Martin's TV specials. Sinatra's fourth and final Timex TV special, '' Welcome Home Elvis'', was broadcast in March 1960, earning massive viewing figures. During the show, he performed a duet with Presley, who sang Sinatra's 1957 hit "
Witchcraft Witchcraft is the use of Magic (supernatural), magic by a person called a witch. Traditionally, "witchcraft" means the use of magic to inflict supernatural harm or misfortune on others, and this remains the most common and widespread meanin ...
" with the host performing the 1956 Presley classic " Love Me Tender". Sinatra had previously been highly critical of
Elvis Presley Elvis Aaron Presley (January 8, 1935 – August 16, 1977) was an American singer and actor. Referred to as the "King of Rock and Roll", he is regarded as Cultural impact of Elvis Presley, one of the most significant cultural figures of the ...
and rock and roll in the 1950s, describing it as a "deplorable, a rancid smelling aphrodisiac" that "fosters almost totally negative and destructive reactions in young people." A
CBS News CBS News is the news division of the American television and radio broadcaster CBS. It is headquartered in New York City. CBS News television programs include ''CBS Evening News'', ''CBS Mornings'', news magazine programs ''CBS News Sunday Morn ...
special about Sinatra's 50th birthday, '' Frank Sinatra: A Man and His Music'', was broadcast on November 16, 1965, and received an Emmy award and a
Peabody Award The George Foster Peabody Awards (or simply Peabody Awards or the Peabodys) program, named for the American businessman and philanthropist George Foster Peabody, George Peabody, honor what are described as the most powerful, enlightening, and in ...
. Continuing his musical collaboration with Jobim and
Ella Fitzgerald Ella Jane Fitzgerald (April25, 1917June15, 1996) was an American singer, songwriter and composer, sometimes referred to as the "First Lady of Song", "Queen of Jazz", and "Lady Ella". She was noted for her purity of tone, impeccable diction, phra ...
in 1967, Sinatra appeared in the TV special, ''
A Man and His Music + Ella + Jobim A, or a, is the first letter and the first vowel letter of the Latin alphabet, used in the modern English alphabet, and others worldwide. Its name in English is '' a'' (pronounced ), plural ''aes''. It is similar in shape to the Ancient ...
'', which was broadcast on CBS on November 13. When Sinatra came out of retirement in 1973, he appeared in a TV special that shared its title with his contemporaneously released album, ''Ol' Blue Eyes Is Back''. In the late 1970s,
John Denver Henry John Deutschendorf Jr. (December 31, 1943 – October 12, 1997), known professionally as John Denver, was an American Country music, country and Folk music, folk singer, songwriter, and actor. He was one of the most popular acoustic m ...
appeared as a guest in the ''Sinatra and Friends'' ABC-TV Special, singing "September Song" as a duet. Sinatra starred as a detective in '' Contract on Cherry Street'' (1977), cited as his "one starring role in a dramatic television film". Ten years later, he made a guest appearance opposite
Tom Selleck Thomas William Selleck (; born January 29, 1945) is an American actor. His breakout role was playing private investigator Thomas Magnum in the television series ''Magnum, P.I.'' (1980–1988), for which he received five Emmy Award nominations fo ...
in ''
Magnum, P.I. ''Magnum, P.I.'' is an American crime drama television series starring Tom Selleck as Thomas Magnum, a private investigator (P.I.) living on Oahu, Hawaii. The series ran from December 11, 1980, to May 1, 1988, during its first-run broadcast on ...
''. Shot in January 1987, the episode aired on CBS on February 25.


Personal life

Sinatra was married to Nancy (née Barbato) from 1939 to 1951. The couple had three children, Nancy (born 1940), Frank Jr. (1944–2016) and
Tina Tina may refer to: People *Tina (given name), people and fictional characters with the given name ''Tina'' Places * Tina, Iran, a village in Khuzestan Province, Iran * Tina, Tunisia, a town in Sfax Governorate, Tunisia * Tina, Guadalcanal, Solom ...
(born 1948). Sinatra met Barbara in Long Branch, New Jersey, in summer 1934 while working as a
lifeguard A lifeguard is a rescuer who supervises the safety and rescue of swimmers, surfers, and other water sports participants such as in a swimming pool, water park, beach, spa, river and lake. Lifeguards are trained in swimming and Cardiopulmonary ...
. He agreed to marry her after an incident at "The Rustic Cabin" that led to his arrest. Sinatra had numerous extramarital affairs, and gossip magazines published details of affairs with women including
Marilyn Maxwell Marvel Marilyn Maxwell (August 3, 1921 – March 20, 1972) was an American actress and entertainer. In a career that spanned the 1940s and 1950s, she appeared in several films and radio programs, and entertained the troops during World War ...
,
Lana Turner Julia Jean "Lana" Turner ( ; February 8, 1921June 29, 1995) was an American actress. Over a career spanning nearly five decades, she achieved fame as both a pin-up model and a film actress, as well as for her highly publicized personal life. ...
and
Joi Lansing Joi Lansing (born Joy Rae Brown; April 6, 1929 – August 7, 1972) was an American model, film and television actress, and nightclub singer. She was noted for her pin-up photos and roles in B-movies, as well as a prominent role in the famous o ...
. Sinatra was married to Hollywood actress
Ava Gardner Ava Lavinia Gardner (December 24, 1922 – January 25, 1990) was an American actress during the Golden Age of Hollywood. She first signed a contract with Metro-Goldwyn-Mayer in 1941 and appeared mainly in small roles until she drew critics' att ...
from 1951 to 1957. It was a turbulent marriage with many well-publicized fights and altercations. The couple formally announced their separation on October 29, 1953, through MGM. Gardner filed for divorce in June 1954, at a time when she was dating matador Luis Miguel Dominguín, but the divorce was not settled until 1957. Sinatra continued to feel very strongly for her, and they remained friends for life. In 1957, Sinatra moved to a home in
Rancho Mirage, California Rancho Mirage is a city in Riverside County, California, United States. The city is a low-density desert community with resorts, golf courses, and country clubs within the Colorado Desert section of the Sonoran Desert. Nestled along the foothil ...
, called The Compound. Sinatra reportedly broke off engagements to
Lauren Bacall Betty Joan Perske (September 16, 1924 – August 12, 2014), professionally known as Lauren Bacall ( ), was an American actress. She was named the AFI's 100 Years...100 Stars, 20th-greatest female star of classic Hollywood cinema by the America ...
in 1958 and
Juliet Prowse Juliet Anne Prowse (25 September 1936 – 14 September 1996) was a British-American dancer and actress whose four-decade career included stage, television and film. She was born in Bombay (today's Mumbai) then of British India, raised in South ...
in 1962. He was romantically linked to
Marilyn Monroe Marilyn Monroe ( ; born Norma Jeane Mortenson; June 1, 1926 August 4, 1962) was an American actress and model. Known for playing comic "Blonde stereotype#Blonde bombshell, blonde bombshell" characters, she became one of the most popular sex ...
, Pat Sheehan, Vikki Dougan, and Kipp Hamilton. Sinatra and
Mia Farrow Maria de Lourdes Villiers "Mia" Farrow ( ; born February 9, 1945) is an American actress. She first gained notice for her role as Allison MacKenzie in the television soap opera ''Peyton Place (TV series), Peyton Place'' and gained further recogn ...
were married on July 19, 1966, and the couple divorced in August 1968. They remained close friends for life, and in a 2013 interview, Farrow said that Sinatra might be the father of her son,
Ronan Farrow Satchel Ronan O'Sullivan Farrow (born December 19, 1987) is an American journalist. The son of actress Mia Farrow and filmmaker Woody Allen, he is known for his investigative reporting on sexual abuse allegations against film producer Harvey Wei ...
(born 1987). In a 2015 ''CBS Sunday Morning'' interview, Nancy Sinatra dismissed the claim as "nonsense". She said that her father had a
vasectomy Vasectomy is an elective surgical procedure that results in male sterilization, often as a means of permanent contraception. During the procedure, the male vasa deferentia are cut and tied or sealed so as to prevent sperm from entering into ...
years before Farrow's birth. Sinatra was married to Barbara Marx from 1976 until his death. The couple married on July 11, 1976, at
Sunnylands Sunnylands is the former Annenberg Estate in Rancho Mirage, California. The property is currently run by The Annenberg Foundation Trust at Sunnylands, a not-for-profit organization. The property was owned by Walter Annenberg, Walter and Leon ...
, in
Rancho Mirage, California Rancho Mirage is a city in Riverside County, California, United States. The city is a low-density desert community with resorts, golf courses, and country clubs within the Colorado Desert section of the Sonoran Desert. Nestled along the foothil ...
, the estate of media magnate
Walter Annenberg Walter Hubert Annenberg (March 13, 1908 – October 1, 2002) was an American businessman, investor, philanthropist, and diplomat. Annenberg owned and operated Triangle Publications, which included ownership of ''The Philadelphia Inquirer' ...
. Sinatra was close friends with
Jilly Rizzo Ermenegildo "Jilly" Rizzo (May 6, 1917 – May 6, 1992) was an American restaurateur and entertainer. Career As a young man, Rizzo worked with his father delivering Italian ice to cafes. Rizzo opened Jilly's Saloon, a lounge on West 49th Stree ...
, songwriter Jimmy Van Heusen, golfer
Ken Venturi Kenneth Paul Venturi (May 15, 1931May 17, 2013) was an American professional golfer and golf broadcaster. In a career shortened by injuries, he won 14 events on the PGA Tour including a major, the U.S. Open in 1964. Shortly before his death in ...
, comedian Pat Henry (comedian), Pat Henry, baseball manager Leo Durocher, and president John F. Kennedy (for whom he organized an United States presidential inaugural balls, inaugural ball with Peter Lawford). In his spare time, he enjoyed listening to classical music. He swam daily in the Pacific Ocean. He often played golf with Venturi at the course in Palm Springs, where he lived in the house Twin Palms he had commissioned from E. Stewart Williams in 1947 He liked painting, reading, and building model railways. Though Sinatra was critical of the church on numerous occasions and had a Albert Einstein's religious views, pantheistic, Einstein-like view of God in his earlier life, he was inducted into the Catholic Sovereign Military Order of Malta in 1976, and he turned to Catholic Church, Catholicism for healing after his mother died in a plane crash in 1977. He died as a practicing Catholic and had a Catholic burial.


Style and personality

Sinatra was known for his immaculate sense of style. He spent lavishly on expensive custom-tailored tuxedos and stylish pin-striped suits, which made him feel wealthy and important and that he was giving his very best to the audience. He was also obsessed with cleanliness—while with the Tommy Dorsey band, he developed the nickname "Lady Macbeth" because of frequent showering and switching his outfits. His deep blue eyes earned him the popular nickname "Ol' Blue Eyes". For Santopietro, Sinatra was the personification of America in the 1950s: "cocky, eye on the main chance, optimistic, and full of the sense of possibility." Barbara Sinatra wrote, "A big part of Frank's thrill was the sense of danger that he exuded, an underlying, ever-present tension only those closest to him knew could be defused with humor." Cary Grant, a friend of Sinatra, stated that Sinatra was the "most honest person he'd ever met", who spoke "a simple truth, without artifice which scared people", and was often moved to tears by his performances. Jo-Caroll Dennison commented that he possessed "great inner strength" and that his energy and drive were "enormous." A workaholic, he reportedly only slept four hours a night on average. Throughout his life, Sinatra had mood swings and bouts of mild to severe Depression (mood), depression, stating to an interviewer in the 1950s that "I have an over-acute capacity for sadness as well as elation." Barbara Sinatra stated that he would "snap at anyone for the slightest misdemeanor", while Van Heusen said that when Sinatra got drunk, it was "best to disappear." Sinatra's mood swings often developed into violence, directed at people he felt had crossed him, particularly journalists who gave him scathing reviews, publicists, and photographers. According to Rojek, he was "capable of deeply offensive behavior that smacked of a persecution complex." He received negative press for fights with Lee Mortimer in 1947, photographer Eddie Schisser in Houston in 1950, Judy Garland's publicist Jim Byron on the Sunset Strip in 1954, and for a confrontation with ''Washington Post'' journalist Maxine Cheshire in 1973, in which he implied that she was a cheap prostitute. His feud with then-''Chicago Sun Times'' columnist Mike Royko began when Royko wrote a column questioning why Chicago police offered free protection to Sinatra when he had his own security. Sinatra wrote an angry letter in response, calling Royko a "pimp" and threatening to "punch you in the mouth" for speculating that he wore a toupée. Sinatra was also known for his generosity, particularly after his comeback. Kelley notes that when Lee J. Cobb nearly died from a heart attack in June 1955, Sinatra flooded him with "books, flowers, delicacies", paid his hospital bills, and visited him daily, telling him that his "finest acting" was yet to come.


Alleged organized-crime links and Cal Neva Lodge

Sinatra became the stereotype of the "tough working-class Italian American", something which he embraced. He said that if it had not been for his interest in music, he would have likely ended up in a life of crime.
Willie Moretti Guarino "Willie" Moretti (February 24, 1894 – October 4, 1951), also known as Willie Moore, was an Italian-American mobster who served as underboss of the Genovese crime family and top member of New Jersey faction under the administration of ...
was Sinatra's godfather and the notorious underboss of the Genovese crime family, and he helped Sinatra in exchange for kickbacks and was reported to have intervened in releasing Sinatra from his contract with Tommy Dorsey. Sinatra was present at the Mafia Havana Conference in 1946, and the press learned of his being there with Lucky Luciano. One newspaper published the headline "Shame, Sinatra". He was reported to be a good friend of mobster Sam Giancana, Kelley quoted Jo-Carrol Silvers that Sinatra "adored" Bugsy Siegel and boasted to friends about him and how many people Siegel had killed. Kelley says that Sinatra and mobster Joseph Fischetti had been good friends from 1938 onward and acted like "Sicilian brothers". She also states that Sinatra and
Hank Sanicola Henry William "Hank" Sanicola (14 June 1914 – 6 October 1974) was an American music manager, publisher, businessman and pianist, best known for his work and association with Frank Sinatra from the late 1930s to the early 1960s. Early life Sanic ...
were financial partners with Mickey Cohen in the gossip magazine ''Hollywood Night Life''. (Johnny) Roselli's membership in the Friars Club in Beverly Hills was sponsored by celebrity singer and Friars Club abbot Frank Sinatra. The FBI kept records amounting to 2,403 pages on Sinatra, who was a natural target with his alleged Mafia ties, his ardent New Deal politics, and his friendship with John F. Kennedy. The FBI kept him under surveillance for almost five decades beginning in the 1940s. The documents include accounts of Sinatra as the target of death threats and extortion schemes. The FBI documented that Sinatra was losing esteem with the Mafia as he grew closer to President Kennedy, whose younger brother Attorney General Robert F. Kennedy was leading a crackdown on organized crime. Sinatra said he was not involved: "Any report that I fraternized with goons or racketeers is a vicious lie." In 1960, Sinatra bought a share in the Cal Neva Lodge & Casino, a casino hotel on the south shore of
Lake Tahoe Lake Tahoe (; Washo language, Washo: ''dáʔaw'') is a Fresh water, freshwater lake in the Sierra Nevada of the Western United States, straddling the border between California and Nevada. Lying at above sea level, Lake Tahoe is the largest a ...
. Sinatra built the Celebrity Room theater, which attracted his show business friends Red Skelton,
Marilyn Monroe Marilyn Monroe ( ; born Norma Jeane Mortenson; June 1, 1926 August 4, 1962) was an American actress and model. Known for playing comic "Blonde stereotype#Blonde bombshell, blonde bombshell" characters, she became one of the most popular sex ...
, Victor Borge, Joe E. Lewis, Lucille Ball,
Lena Horne Lena Mary Calhoun Horne (June 30, 1917 – May 9, 2010) was an American singer, actress, dancer and civil rights activist. Horne's career spanned more than seventy years and covered film, television and theatre. Horne joined the chorus of the C ...
,
Juliet Prowse Juliet Anne Prowse (25 September 1936 – 14 September 1996) was a British-American dancer and actress whose four-decade career included stage, television and film. She was born in Bombay (today's Mumbai) then of British India, raised in South ...
, the McGuire Sisters, and others. By 1962, he reportedly held a 50-percent share in the hotel. Sinatra's gambling license was temporarily suspended by the Nevada Gaming Control Board in 1963 after Giancana was spotted on the premises. Due to ongoing pressure from the FBI and Nevada Gaming Commission on mobster control of casinos, Sinatra agreed to give up his share in Cal Neva and the Sands. That year, his son Frank Sinatra Jr.#Kidnapping, Frank Jr. was kidnapped but was eventually released unharmed. Sinatra's gambling license was restored in February 1981, following support from Ronald Reagan.


Political views and activism

Sinatra held varied political views throughout his life. His mother, Dolly, was a Democratic Party ward leader. After meeting President Franklin D. Roosevelt in 1944, he subsequently heavily campaigned for the Democrats in the 1944 United States presidential election, 1944 presidential election. According to Jo Carroll Silvers, in his younger years, Sinatra had "ardent liberal" sympathies and was "so concerned about poor people that he was always quoting Henry A. Wallace, Henry Wallace." He was outspoken against racism, particularly toward black people and Italians, from a young age. In the early 1950s, he was among those who campaigned to combine the racially segregated musicians' unions in Los Angeles. In November 1945, Sinatra was invited by the mayor of Gary, Indiana, to try to settle a strike by white students of Froebel High School against the "Pro-Negro" policies of the new principal. His comments, while praised by liberal publications, led to accusations by some that he was a Communism, communist, which he denied. In the 1948 United States presidential election, 1948 presidential election, Sinatra actively campaigned for President Harry S. Truman. In 1952 and 1956, he campaigned for Adlai Stevenson II, Adlai Stevenson. Of all the U.S. presidents he associated with during his career, he was closest to John F. Kennedy. Sinatra often invited Kennedy to Hollywood and Las Vegas, and the two would womanize and enjoy parties together. In January 1961, Sinatra and Peter Lawford organized the United States presidential inaugural balls, Inaugural Gala in Washington, D.C., held on the evening before President Kennedy was sworn into office. After taking office, Kennedy distanced himself from Sinatra due partly to Sinatra's ties with the Mafia. In 1962, Sinatra was snubbed by the President as, during his visit to his Palm Springs, California, Palm Springs, Kennedy stayed with the Republican Bing Crosby instead of Sinatra, citing FBI concerns about the latter's alleged connections to organized crime. Sinatra had spared no expense upgrading the facilities at his home in anticipation of the President's visit, fitting it with a heliport, which he smashed with a sledgehammer after the rejection. Despite the snub, when he learned of Kennedy's assassination he reportedly sobbed in his bedroom for three days. Sinatra worked with Hubert H. Humphrey in 1968, and remained a supporter of the Democratic Party until the early 1970s. Although still a registered Democrat, Sinatra endorsed Republican Party (United States), Republican Ronald Reagan for a second term as Governor of California in 1970. He officially changed allegiance in July 1972 when he supported
Richard Nixon Richard Milhous Nixon (January 9, 1913April 22, 1994) was the 37th president of the United States, serving from 1969 until Resignation of Richard Nixon, his resignation in 1974. A member of the Republican Party (United States), Republican ...
in the 1972 United States presidential election, 1972 presidential election. In the 1980 United States presidential election, 1980 presidential election, Sinatra donated $4million to Ronald Reagan's campaign. Sinatra arranged Reagan's Presidential gala, as he had done for Kennedy. In 1985, Reagan presented Sinatra with the
Presidential Medal of Freedom The Presidential Medal of Freedom is the highest civilian award of the United States, alongside the Congressional Gold Medal. It is an award bestowed by decision of the president of the United States to "any person recommended to the President ...
, remarking, "His love of country, his generosity for those less fortunate... make him one of our most remarkable and distinguished Americans." In June 1984, Sinatra performed at the State Dinner in the White House honoring President of Sri Lanka, Sri Lankan President J. R. Jayewardene, J. R. Jayawardena at the invitation of Reagan. Santopietro notes that Sinatra was a "lifelong sympathizer with Frank Sinatra and Jewish activism, Jewish causes." He was awarded the Hollzer Memorial Award by the History of the Jews in Los Angeles, Los Angeles Jewish Community in 1949. He gave a series of concerts in Israel in 1962 and donated his entire $50,000 fee for appearing in a cameo role in ''Cast a Giant Shadow'' (1966) to the Youth Center in Jerusalem. On November 1, 1972, he raised $6.5million in bond pledges for Israel, and was given the Medallion of Valor for his efforts. The Frank Sinatra Student Center at the
Hebrew University of Jerusalem The Hebrew University of Jerusalem (HUJI; ) is an Israeli public university, public research university based in Jerusalem. Co-founded by Albert Einstein and Chaim Weizmann in July 1918, the public university officially opened on 1 April 1925. ...
was dedicated in his name in 1978. From his youth, Sinatra displayed sympathy for black Americans and worked both publicly and privately all his life to help the struggle for equal rights. He blamed racial prejudice on the parents of children. Sinatra played a major role in the Desegregation in the United States, desegregation of Nevada hotels and casinos in the 1950s and 1960s. On January 27, 1961, Sinatra played a benefit show at Carnegie Hall for Martin Luther King Jr. and led his fellow Rat Pack members and Reprise label mates in boycotting hotels and casinos that refused entry to black patrons and performers. According to his son, Frank Jr., King sat weeping in the audience at one of his father's concerts in 1963 as Sinatra sang "
Ol' Man River "Ol' Man River" is a show tune from the 1927 musical '' Show Boat'' with music by Jerome Kern and lyrics by Oscar Hammerstein II, who wrote the song in 1925. The song contrasts the struggles and hardships of African Americans with the endless, ...
", a song from the musical ''Show Boat'' that is sung by a black American stevedore. When he changed his political affiliations in 1970, Sinatra became less outspoken on racial issues. Though he did much towards civil rights causes, it did not stop the occasional racial jibe from him and the other Rat Pack members toward Davis at concerts.


Death and funeral

During the final years of his life, Sinatra was in ill health and was frequently hospitalized for Cardiovascular disease, heart and breathing problems, high blood pressure, pneumonia, and bladder cancer. He made no public appearances following a Myocardial infarction, heart attack in February 1997. A year later, on the night of May 14, 1998, Sinatra died in his sleep after suffering another heart attack at Cedars-Sinai Medical Center in Los Angeles, with his wife Barbara at his side. He was 82. Barbara encouraged Sinatra to "fight" while attempts were made to stabilize him, and reported that his final words were, "I'm losing." Sinatra's daughter, Tina, later wrote that she and her siblings had not been notified of their father's final hospitalization, and it was her belief that "the omission was deliberate. Barbara would be the grieving widow ''alone'' at her husband's side." The night after Sinatra's death, the lights on the
Empire State Building The Empire State Building is a 102-story, Art Deco-style supertall skyscraper in the Midtown South neighborhood of Manhattan, New York City, United States. The building was designed by Shreve, Lamb & Harmon and built from 1930 to 1931. Its n ...
were turned blue, the lights at the Las Vegas Strip were dimmed in his honor, and the casinos stopped spinning for one minute. Significant increases in recording sales worldwide were reported by ''Billboard'' in the month of his death. Sinatra's funeral was held at the Church of the Good Shepherd (Beverly Hills, California), Church of the Good Shepherd in Beverly Hills, California, on May 20, 1998, with 400 mourners in attendance and thousands of fans outside. Gregory Peck,
Tony Bennett Anthony Dominick Benedetto (August 3, 1926 – July 21, 2023), known professionally as Tony Bennett, was an American jazz and traditional pop singer. He received many accolades, including 20 Grammy Awards, a Grammy Lifetime Achievement Award, ...
, and Sinatra's son, Frank Jr., addressed the mourners, who included many people from entertainment. Sinatra was buried in a blue business suit; his grave, adorned with mementos from family members, was next to his parents in Desert Memorial Park in Cathedral City, California. The phrases "The Best Is Yet to Come", and "Beloved Husband & Father" were placed on Sinatra's modest grave marker. Sinatra's gravestone was changed to read "Sleep Warm, Poppa", due to damage caused to the original gravestone under mysterious circumstances, according to the magazine ''Palm Springs Life''.


Legacy and honors

Robert Christgau Robert Thomas Christgau ( ; born April 18, 1942) is an American music journalist and essayist. Among the most influential music critics, he began his career in the late 1960s as one of the earliest professional rock critics and later became a ...
referred to Sinatra as "the greatest singer of the 20th century". His popularity is matched only by
Elvis Presley Elvis Aaron Presley (January 8, 1935 – August 16, 1977) was an American singer and actor. Referred to as the "King of Rock and Roll", he is regarded as Cultural impact of Elvis Presley, one of the most significant cultural figures of the ...
,
the Beatles The Beatles were an English Rock music, rock band formed in Liverpool in 1960. The core lineup of the band comprised John Lennon, Paul McCartney, George Harrison and Ringo Starr. They are widely regarded as the Cultural impact of the Beatle ...
, and Michael Jackson. For Santopietro, Sinatra was the "greatest male pop singer in the history of America", who amassed "unprecedented power onscreen and off", and "seemed to exemplify the common man, an ethnic twentieth-century American male who reached the 'top of the heap', yet never forgot his roots." Santopietro argues that Sinatra created his world, which he was able to dominate—his career was centered around power, perfecting the ability to capture an audience. Gus Levene commented that Sinatra's strength was that when it came to lyrics, telling a story musically, Sinatra displayed a "genius" ability and feeling, which with the "rare combination of voice and showmanship" made him the "original singer" which others who followed most tried to emulate. George Roberts (trombonist), George Roberts, a trombonist in Sinatra's band, remarked that Sinatra had a "charisma, or whatever it is about him, that no one else had." Biographer Arnold Shaw considered that "If Las Vegas had not existed, Sinatra could have invented it." He quoted reporter James Bacon (author), James Bacon in saying that Sinatra was the "swinging image on which the town is built", adding that no other entertainer quite "embodied the glamour" associated with Las Vegas. Sinatra is seen as one of the icons of the 20th century, and has three stars on the Hollywood Walk of Fame for his work in film and music. In Sinatra's native Hoboken, New Jersey, Hoboken, he was awarded the Freedom of the City, Key to the City by Mayor of Hoboken, New Jersey, Mayor Fred M. De Sapio on October 30, 1947. In 2003, the city's main post office was rededicated in his honor. A bronze plaque, placed two years before Sinatra's death in 1998, marks the site of the house where he was born. There is also a marker in front of Hoboken Historical Museum, which has artifacts from his life and conducts Sinatra walking tours. Frank Sinatra Drive runs parallel to the Hudson River Waterfront Walkway. On the waterfront is Frank Sinatra Park, where a bronze plaque was placed in 1989 upon its opening. In the Frank Sinatra Park, a tall bronze statue of Frank Sinatra, statue of Sinatra was dedicated in 2021 on December 12, Sinatra's birthday. A residence hall at Montclair State University in New Jersey was named in his honor. Other buildings named for Sinatra include the Frank Sinatra School of the Arts in Astoria, Queens, the Frank Sinatra International Student Center at Israel's Hebrew University in Jerusalem dedicated in 1978, and the Frank Sinatra Hall at the USC School of Cinematic Arts in Los Angeles, California, dedicated in 2002. Wynn Resorts' Encore Las Vegas resort features a restaurant dedicated to Sinatra which opened in 2008. There are several streets and roads named in honor of Frank Sinatra in several states of the U.S. Various items of memorabilia from Sinatra's life and career, such as Frank Sinatra's awards, gold records, and various personal items, are displayed at University of Southern California, USC's Frank Sinatra Hall in Los Angeles and at Wynn Resort's Sinatra restaurant in Las Vegas. The United States Postal Service issued a 42-cent stamp in honor of Sinatra in May 2008, commemorating the tenth anniversary of his death. The United States Congress passed a resolution on May 20, 2008, designating May 13 as Frank Sinatra Day. Sinatra received three Honorary Degrees during his lifetime. In May 1976, he was invited to speak at the University of Nevada, Las Vegas graduation commencement held at Sam Boyd Stadium. It was at this commencement that he was bestowed an Honorary Doctorate litterarum humanarum by the university. During his speech, Sinatra stated that his education had come from "School of Hard Knocks, the school of hard knocks" and that "this is the first educational degree I have ever held in my hand. I will never forget what you have done for me today". In 1984 and 1985, Sinatra received an Honorary Doctorate of Fine Arts from Loyola Marymount University and an Honorary Doctorate of Engineering from the
Stevens Institute of Technology Stevens Institute of Technology is a Private university, private research university in Hoboken, New Jersey. Founded in 1870, it is one of the oldest technological universities in the United States and was the first college in America solely de ...
. In 2023, ''Rolling Stone'' ranked Sinatra at No. 19 on their list of the 200 Greatest Singers of All Time. In 2024, a new road in North Bristol was named ''Sinatra Way'', to commemorate Sinatra's 1953 visit to Frenchay Hospital, which used to sit at the site of a new housing development.


Tribute albums to Sinatra

* ''A Jazz Portrait of Frank Sinatra'' by Oscar Peterson (1959) * ''Very Sinatra'' by Ruby Braff (1981) * ''Perfectly Frank'' by
Tony Bennett Anthony Dominick Benedetto (August 3, 1926 – July 21, 2023), known professionally as Tony Bennett, was an American jazz and traditional pop singer. He received many accolades, including 20 Grammy Awards, a Grammy Lifetime Achievement Award, ...
(1992) * ''Voices in Standard'' by The Four Freshmen (1994) * ''As I Remember It'' by Frank Sinatra, Jr. (1996) * ''Manilow Sings Sinatra'' by Barry Manilow (1998) * ''Sinatraland'' by Patrick Williams (composer), Patrick Williams and His Big Band (1998) * ''Blue Eyes Plays Ol' Blue Eyes'' by Si Zentner & Orchestra (1998) * ''Keely Sings Sinatra'' by Keely Smith (2001) * ''Michael Andrew Pays Tribute to Frank Sinatra'' by Michael Andrew (singer), Michael Andrew (2002) * Frank (Amy Winehouse album), ''Frank'' by Amy Winehouse [2003] * ''Steve Lawrence Sings Sinatra'' by Steve Lawrence (2003) * ''Plays Sinatra His Way'' by Joey DeFrancesco (2004) * ''Allow Us to Be Frank'' by Westlife (2004) * ''Songs of Sinatra'' by Steve Tyrell (2005) * ''Blue Eyes Meets Bed-Stuy'' The Notorious B.I.G. & Frank Sinatra by Jon Moskowitz and Dj Cappel & Smitty (2005) * ''L'allieva'' by Mina (Italian singer), Mina (2005) * ''Bolton Swings Sinatra'' by Michael Bolton (2006) * ''Dear Mr. Sinatra'' by John Pizzarelli (2006) * ''Ray Stevens Sings Sinatra...Say What??'' by Ray Stevens (2008) * ''His Way, Our Way'' by various artists (2009) * ''Cauby Sings Sinatra'' by Cauby Peixoto (2010) * ''Sin-Atra'' a heavy metal tribute by various artists (2011) *''Daniel Boaventura Sings Frank Sinatra (Ao Vivo)'' (2015) * ''Let's Be Frank'' by Trisha Yearwood (2018) * ''My Way (Willie Nelson album), My Way'' by Willie Nelson (2018) * ''That%27s Life (Willie Nelson album), That’s Life'' by Willie Nelson (2021)


Film, television and stage portrayals

A television miniseries based on Sinatra's life, titled ''Sinatra (miniseries), Sinatra'', was aired by CBS in 1992. The series was directed by James Steven Sadwith, who won an Emmy Award for Primetime Emmy Award for Outstanding Directing for a Limited Series, Movie, or Dramatic Special, Outstanding Individual Achievement in Directing for a Miniseries or a Special and starred Philip Casnoff as Sinatra. ''Sinatra'' was written by Abby Mann and Philip Mastrosimone and produced by Sinatra's daughter, Tina. Sinatra has subsequently been portrayed on screen by Ray Liotta (''The Rat Pack (film), The Rat Pack'', 1998), James Russo (''Stealing Sinatra'', 2003), Dennis Hopper (''The Night We Called It a Day (film), The Night We Called It a Day'', 2003), and Robert Knepper (''My Way (2012 film), My Way'', 2012), and spoofed by Joe Piscopo and Phil Hartman on ''Saturday Night Live''. A biographical film directed by Martin Scorsese has long been planned. A 1998 episode of the BBC documentary series ''Arena (UK TV series), Arena'', ''The Voice of the Century'', focused on Sinatra. Alex Gibney directed a four-part biographical series on Sinatra, ''All or Nothing at All'', for HBO in 2015. A musical tribute was aired on
CBS CBS Broadcasting Inc., commonly shortened to CBS (an abbreviation of its original name, Columbia Broadcasting System), is an American commercial broadcast television and radio network serving as the flagship property of the CBS Entertainme ...
television in December 2015 to mark Sinatra's centenary. Sinatra was also portrayed by Rico Simonini in the 2018 feature film ''Frank & Ava'', which is based on a play by Willard Manus. Creed (band), Creed singer Scott Stapp also portrayed Sinatra in the 2024 feature film ''Reagan (2024 film), Reagan'', a biopic of U.S. President Ronald Reagan. Martin Scorsese planned to make a film on Sinatra and his second wife Ava Gardner. Sinatra believed that Johnny Fontane, a mob-associated singer in Mario Puzo's novel ''The Godfather (novel), The Godfather'' (1969), was based on him. Puzo wrote in 1972 that when the author and singer met in Chasen's, Sinatra "started to shout abuse", calling Puzo a "pimp" and threatening violence. Francis Ford Coppola, director of the The Godfather, film adaptation, said in the audio commentary that "Obviously Johnny Fontane was inspired by a kind of Frank Sinatra character". In 2023, a biopic jukebox stage musical titled ''Sinatra: The Musical'' by Joe DiPietro premiered at the Birmingham Repertory Theatre starring Tony Award-winning actor Matt Doyle (actor), Matt Doyle as Sinatra.


Discography

Studio albums * '' The Voice of Frank Sinatra'' (1946) * '' Songs by Sinatra'' (1947) * ''
Christmas Songs by Sinatra ''Christmas Songs by Sinatra'' is the third studio album by the American singer Frank Sinatra. It was released on October 4, 1948 as a 78 rpm album set of four 78 rpm records in an actual album and as a 10" LP record (CL 6019) featuring a colle ...
'' (1948) * '' Frankly Sentimental'' (1949) * '' Dedicated to You'' (1950) * ''Swing and Dance with Frank Sinatra, Sing and Dance with Frank Sinatra'' (1950) * '' Songs for Young Lovers'' (1954) * '' Swing Easy!'' (1954) * ''
In the Wee Small Hours ''In the Wee Small Hours'' is the ninth studio album by American singer Frank Sinatra, released on April 25, 1955, by Capitol Records. Produced by Voyle Gilmore with arrangements by Nelson Riddle, the album's songs deal with themes such as i ...
'' (1955) * '' Songs for Swingin' Lovers!'' (1956) * '' Close to You'' (1957) * ''
A Swingin' Affair! ''A Swingin' Affair!'' is the twelfth studio album by Frank Sinatra. It is sometimes mentioned as the sequel to ''Songs for Swingin' Lovers''. "The Lady Is a Tramp" was bumped from the original album and replaced with "No One Ever Tells You" ...
'' (1957) * '' Where Are You?'' (1957) * ''A Jolly Christmas from Frank Sinatra'' (1957) * '' Come Fly with Me'' (1958) * ''
Frank Sinatra Sings for Only the Lonely ''Frank Sinatra Sings for Only the Lonely'' (also known as ''Sings for Only the Lonely'' or simply ''Only the Lonely'') is the fifteenth studio album by American singer Frank Sinatra. It was released on September 8, 1958, through Capitol Records. ...
'' (1958) * '' Come Dance with Me!'' (1959) * '' No One Cares'' (1959) * ''
Nice 'n' Easy ''Nice 'n' Easy'' is the eighteenth studio album by Frank Sinatra, released on July 25, 1960. All the songs, with the notable exception of the title song, are sung as ballads and were arranged and conducted by Nelson Riddle. The title song was ...
'' (1960) * ''
Sinatra's Swingin' Session!!! ''Sinatra's Swingin' Session!!!'' is the nineteenth studio album by Frank Sinatra, released on January 3, 1961. Six of the tracks on the album are re-recordings of a batch of songs that Sinatra had previously recorded on the Columbia album, ...
'' (1961) * ''
Ring-a-Ding-Ding! ''Ring-a-Ding-Ding!'' is the twentieth studio album by Frank Sinatra, released on May 7, 1961. It was the inaugural record on Sinatra's Reprise label and, as the initial concept was "an album without ballads", it consisted only of uptempo swi ...
'' (1961) * ''Come Swing with Me!'' (1961) * ''Sinatra Swings, Swing Along With Me'' (1961) * ''I Remember Tommy'' (1961) * '' Sinatra and Strings'' (1962) * ''
Point of No Return The point of no return (PNR or PONR) is the point beyond which one must continue on one's current course of action because turning back is no longer possible, being too dangerous, physically difficult, or prohibitively expensive to be undertaken. ...
'' (1962) * ''Sinatra and Swingin' Brass'' (1962) * ''All Alone (Frank Sinatra album), All Alone'' (1962) * ''Sinatra Sings Great Songs from Great Britain'' (1962) * '' The Concert Sinatra'' (1963) * ''Sinatra's Sinatra'' (1963) * ''Sinatra Sings Days of Wine and Roses, Moon River, and Other Academy Award Winners'' (1964) * '' Softly, as I Leave You'' (1964) * '' September of My Years'' (1965) * ''Sentimental Journey (song), Sentimental Journey'' (1965) * ''My Kind of Broadway'' (1965) * '' A Man and His Music'' (1965) * ''Moonlight Sinatra'' (1966) * ''Strangers in the Night (Frank Sinatra album), Strangers in the Night'' (1966) * '' That's Life'' (1966) * ''
The World We Knew ''The World We Knew'', also known as ''Frank Sinatra'', is a 1967 studio album by American singer Frank Sinatra. The album's title track reached No. 30 on the US ''Billboard'' Hot 100 chart and #1 on the Easy Listening chart in 1967. Its second ...
'' (1967) * ''Cycles (Frank Sinatra album), Cycles'' (1968) * ''My Way (Frank Sinatra album), My Way'' (1969) * ''A Man Alone (album), A Man Alone'' (1969) * '' Watertown'' (1970) * ''
Ol' Blue Eyes Is Back ''Ol' Blue Eyes Is Back'' is a 1973 studio album by American singer Frank Sinatra. Sinatra returned from his brief retirement with ''Ol' Blue Eyes Is Back''. Released amidst a whirlwind of publicity, the album was a commercial success, earnin ...
'' (1973) * ''Some Nice Things I've Missed'' (1974) * '' Trilogy: Past Present Future'' (1980) * '' She Shot Me Down'' (1981) * '' L.A. Is My Lady'' (1984) * '' Duets'' (1993) * '' Duets II'' (1994) Collaboration albums * ''Sinatra–Basie: An Historic Musical First'' with Count Basie (1962) * '' America, I Hear You Singing'' with Bing Crosby and Fred Waring (1964) * '' It Might as Well Be Swing'' with Count Basie (1964) * ''12 Songs of Christmas (Frank Sinatra, Bing Crosby and Fred Waring album), 12 Songs of Christmas'' with Bing Crosby and Fred Waring (1964) * ''
Francis Albert Sinatra & Antonio Carlos Jobim ''Francis Albert Sinatra & Antonio Carlos Jobim'' is a 1967 album by Frank Sinatra and Antônio Carlos Jobim. The tracks were arranged and conducted by Claus Ogerman, accompanied by a studio orchestra. Along with Jobim's original compositions, t ...
'' with Antonio Carlos Jobim (1967) * '' Francis A. & Edward K.'' with Duke Ellington (1968) * ''The Sinatra Family Wish You a Merry Christmas'' with Frank Sinatra Jr., Nancy Sinatra and Tina Sinatra (1968) * '' Sinatra & Company'' with Antonio Carlos Jobim (1971)


See also

* Frank Sinatra bibliography * Frank Sinatra's recorded legacy * The Frank Sinatra Show (radio program), ''The Frank Sinatra Show'' (radio program)


Notes


References


Sources

* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *


Further reading

* Freedland, Michael (1998). ''All the Way: A Biography of Frank Sinatra''. St. Martin's Press. * Kaplan, James (2015). ''Sinatra: The chairman''. New York: Doubleday. * Pickard, Roy (1994). ''Frank Sinatra at the Movies''. Hale.


External links

*
Sinatra family website

Frank Sinatra webradio
*
Biography
at New Jersey Hall of Fame * *
Frank Sinatra
at FBI Records: The Vault
''The Sinatra Report'', a special section of Billboard's November 20, 1965, issue – beginning immediately after page 34Sinatra in Retrospect; No. 1; The Young Sinatra; Parts 1 and 2
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