"A Pirate Looks at Forty" is a song written and performed by American singer-songwriter

Jimmy Buffett James William Buffett (born December 25, 1946) is an American singer-songwriter, musician, author, and businessman. He is best known for his music, which often portrays an "island escapism" lifestyle. Together with his Coral Reefer Band, Buffet ...

. It was first released on his 1974 album ''

A1A State Road A1A (SR A1A) is a major north–south Florida State Road that runs along the Atlantic Ocean, from Key West at the southern tip of Florida, to Fernandina Beach, just south of Georgia on Amelia Island. It is the main road throug ...

'' and "Presents to Send You" is the

B-side The A-side and B-side are the two sides of phonograph records and cassettes; these terms have often been printed on the labels of two-sided music recordings. The A-side usually features a recording that its artist, producer, or record compan ...

of the single. Buffett wrote the song about Phillip Clark, at the Chart Room where Buffett first performed after his move to

Key West, Florida Key West ( es, Cayo Hueso) is an island in the Straits of Florida, within the U.S. state of Florida. Together with all or parts of the separate islands of Sigsbee Park, Dredgers Key, Fleming Key, Sunset Key, and the northern part of Stock Isla ...

. The song contains the bittersweet confession of a modern-day, washed-up drug smuggler as he looks back on the first 40 years of his life, expresses lament that his preferred vocation of

piracy Piracy is an act of robbery or criminal violence by ship or boat-borne attackers upon another ship or a coastal area, typically with the goal of stealing cargo and other valuable goods. Those who conduct acts of piracy are called pirates, v ...

on the high seas was long gone by the time he was born, and ponders his future. For radio play, the song was shortened by deleting the fourth verse for the single release. ''

Cash Box ''Cashbox'', also known as ''Cash Box'', was an American music industry trade magazine, originally published weekly from July 1942 to November 1996. Ten years after its dissolution, it was revived and continues as ''Cashbox Magazine'', an online ...

'' said the song has "an almost

reggae Reggae () is a music genre that originated in Jamaica in the late 1960s. The term also denotes the modern popular music of Jamaica and its diaspora. A 1968 single by Toots and the Maytals, " Do the Reggay" was the first popular song to use ...

progression, fine guitar playing and lead solo, ndmoving lyrics." ''

Record World ''Record World'' magazine was one of the three main music industry trade magazines in the United States, along with '' Billboard'' and '' Cashbox''. It was founded in 1946 under the name ''Music Vendor'', but in 1964 it was changed to ''Record Wo ...

'' said that "This limitless piece of demographic dauntlessness should ship him out of port under more steam than anything since '

Come Monday "Come Monday" is a song written and recorded by American singer-songwriter Jimmy Buffett. It was first released on his 1974 album '' Living & Dying in ¾ Time''. Content Buffett wrote the song to his wife while he was on tour. At a live perfo ...

.'" The song is one of Buffett's more popular, and is part of " The Big 8" that he played at almost all of his concerts, and always during the second set.

Chart performance

Cover versions

Ian McNabb Robert Ian McNabb (born 3 November 1960) is an English singer-songwriter and musician. Previously the frontman of The Icicle Works, McNabb has since embarked on a solo career and performed with Ringo Starr, Neil Young/Crazy Horse, Mike Scott ...

included a cover on his CD single "I'm Game" in 1993 which was taken from his solo album "Truth and Beauty". Jack Johnson has been known to cover this song in many of his smaller concerts. It was officially released on the soundtrack to '' The September Sessions'' in 2002.

Roger Creager Roger Creager (born July 25, 1971) is an American Texas country music singer and songwriter from Corpus Christi, Texas. Biography Creager aspired to become a country music singer since he was six years old. He started learning how to play pia ...

, a prominent

Texas Country Texas country music (more popularly known just as Texas country or Texas music) is a rapidly growing subgenre of country music from Texas. Texas country is a unique style of Western music and is often associated with other distinct neighboring s ...

performer, covers this song as well and is featured on his live album ''Live Across Texas''.

Bob Dylan Bob Dylan (legally Robert Dylan, born Robert Allen Zimmerman, May 24, 1941) is an American singer-songwriter. Often regarded as one of the greatest songwriters of all time, Dylan has been a major figure in popular culture during a career sp ...

and

Joan Baez Joan Chandos Baez (; born January 9, 1941) is an American singer, songwriter, musician, and activist. Her contemporary folk music often includes songs of protest and social justice. Baez has performed publicly for over 60 years, releasing more ...

performed the song during their 1982 reunion performance at the Peace Sunday rally in Pasadena, California. Dave Matthews alongside Jack Johnson performed the song at Kokua Benefit Concert at the Waikiki Shell in Honolulu in 2008.

Dave Matthews Band Dave Matthews Band (also known by the initials DMB) is an American rock band formed in Charlottesville, Virginia, in 1991. The band's founding members were singer-songwriter and guitarist Dave Matthews, bassist Stefan Lessard, drummer and bac ...

performed the song to open their show at The Gorge Amphitheatre the day after Buffett's death in 2023. Songwriter/Musician T.J. O'Neill collaborated with long-time friend

Stick Figure A stick figure, also known as a stickman, is a very simple drawing of a person or an animal, composed of a few lines, curves, and dots. On a stick figure, the head is most often represented by a circle, which can be either a solid color or som ...

on the song which was his first single in 2019. It also featured reggae artists KBong and Johnny Cosmic. The music video was shot live on location at a resort in

Mexico Mexico (Spanish: México), officially the United Mexican States, is a country in the southern portion of North America. It is bordered to the north by the United States; to the south and west by the Pacific Ocean; to the southeast by Guatema ...

with thousands of fans surrounding the singers while performing.

Notes and references

1974 songs Jimmy Buffett songs Dunhill Records singles Songs about pirates Songs about old age Songs about drugs Songs written by Jimmy Buffett {{1970s-song-stub