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Robert Underdunk Terwilliger Jr., PhD, better known as Sideshow Bob, is a
recurring character A recurring character is a fictional character, usually in a prime time TV series, who frequently appears from time to time during the series' run. Recurring characters often play major roles in more than one episode, sometimes being the main foc ...
in the animated television series ''
The Simpsons ''The Simpsons'' is an American animated sitcom created by Matt Groening for the Fox Broadcasting Company. The series is a satirical depiction of American life, epitomized by the Simpson family, which consists of Homer Simpson, Homer, Marge ...
''. He is voiced by
Kelsey Grammer Allen Kelsey Grammer (born February 21, 1955) is an American actor and producer. He gained notoriety and acclaim for his role as psychiatrist Dr. Frasier Crane on the NBC sitcom ''Cheers'' (1984-1993) and its spin-off ''Frasier'' (1993-2004), f ...
and first appeared in the episode "
The Telltale Head "The Telltale Head" is the eighth episode of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on February 25, 1990. It was written by Al Jean, Mike Reiss, Sam Simon and Matt Gr ...
". Bob is a self-proclaimed genius who is a graduate of
Yale University Yale University is a private research university in New Haven, Connecticut. Established in 1701 as the Collegiate School, it is the third-oldest institution of higher education in the United States and among the most prestigious in the worl ...
and a champion of
high culture High culture is a subculture that emphasizes and encompasses the cultural objects of aesthetic value, which a society collectively esteem as exemplary art, and the intellectual works of philosophy, history, art, and literature that a society co ...
, including the adoption of a transatlantic accent, similar to that of Grammer's portrayal of Dr. Frasier Crane from the sitcoms ''
Cheers ''Cheers'' is an American sitcom television series that ran on NBC from September 30, 1982, to May 20, 1993, with a total of 275 half-hour episodes across 11 seasons. The show was produced by Charles/Burrows/Charles Productions in association w ...
'' and ''
Frasier ''Frasier'' () is an American television sitcom that was broadcast on NBC for 11 seasons. It premiered on September 16, 1993, and ended on May 13, 2004. The program was created and produced by David Angell, Peter Casey, and David Lee (as Grub ...
''. He began his career as a sidekick on
Krusty the Clown Herschel Shmoikel Pinchas Yerucham Krustofsky (; ) better known by his stage name Krusty the Clown (sometimes spelled as Krusty the Klown), is a recurring character on the animated television series ''The Simpsons''. He is voiced by Dan Caste ...
's television show, but after enduring constant abuse, Bob framed his employer for armed robbery in "
Krusty Gets Busted "Krusty Gets Busted" is the twelfth and penultimate episode of the first season of the American animated television series ''The Simpsons''. It originally aired on the Fox Network in the United States on April 29, 1990.Bart Simpson Bartholomew JoJo "Bart" Simpson is a fictional character in the American animated television series ''The Simpsons'' and part of the Simpson family. He is voiced by Nancy Cartwright and first appeared on television in ''The Tracey Ullman Show'' ...
, and sent to prison. Bob started seeking revenge against Bart while in prison, and the two became feuding arch-enemies. Bob made his second major appearance in season three's " Black Widower"; the writers echoed the premise of Wile E. Coyote chasing the Road Runner by having Bob unexpectedly insert himself into Bart's life, threatening to disrupt and end it through murder. Starting with that appearance and thereafter, Bob has assumed the role on ''The Simpsons'' of an evil genius. Episodes in which he is a central character typically involve Sideshow Bob being released from prison and executing an elaborate revenge plan, usually foiled by Bart and
Lisa Lisa or LISA may refer to: People People with the mononym * Lisa Lisa (born 1967), American actress and lead singer of the Cult Jam * Lisa (Japanese musician, born 1974), stylized "LISA", Japanese singer and producer * Lisa Komine (born 1978), ...
. His plans often involve death and destruction, usually targeted at Bart or, less often, Krusty, though he starts targeting the entire Simpson family in
season 17 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
. In
season 27 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, however, during the first segment of "
Treehouse of Horror XXVI "Treehouse of Horror XXVI" is the fifth episode of the twenty-seventh season of the American animated television series ''The Simpsons'', the 26th episode in the ''Treehouse of Horror'' series of Halloween specials, and the 579th episode of the s ...
", entitled "Wanted: Dead, Then Alive", Bob finally gets his wish of killing Bart, commenting that he spent 24 years trying to kill a ten-year-old child; however, he becomes bored with Bart dead, so he brings him back to life so that he can repeatedly kill Bart over and over again. Despite his villainous deeds, Sideshow Bob shares some personality traits of Grammer's character Frasier Crane, and he has been described as "Frasier pickled in arsenic". Several parallels have been explicitly drawn in ''The Simpsons'' between Bob and Frasier Crane—Bob's brother Cecil and his father were played by
David Hyde Pierce David Hyde Pierce (born April 3, 1959) is an American actor and director of stage, film and television. He starred as psychiatrist Dr. Niles Crane on the NBC sitcom ''Frasier'' from 1993 to 2004, and won four Primetime Emmy Awards and a Screen ...
and
John Mahoney Charles John Mahoney (June 20, 1940 – February 4, 2018) was an English-born American actor. He was known for playing Martin Crane on the NBC sitcom ''Frasier'' (1993–2004), and won a Screen Actors Guild Award for the role in 2000. Mahoney ...
, respectively, echoing the roles they played in ''Frasier''. Grammer, who based Bob's voice on that of actor
Ellis Rabb Ellis W. Rabb (June 20, 1930 – January 11, 1998) was an American actor and director who in 1959 formed the Association of Producing Artists, a theatre company that brought new works and noteworthy revivals to Broadway and to regional theatres. ...
, has been praised for his portrayals of the character. In 2006, he won an Emmy for Outstanding Voice-Over Performance for his work in the episode "The Italian Bob". As of December 15, 2019, Bob has appeared in more than 40 episodes, had speaking appearances in 23 of these, and been featured as the main character in 14; the most recent of the latter, " Bobby, It's Cold Outside", aired on said date during the 31st season. In addition to his recurring role in the series, Sideshow Bob has made several appearances in other ''Simpsons'' media and is mentioned in several more episodes. He appears in the ''Simpsons Comics'', the 2007 video game ''
The Simpsons Game ''The Simpsons Game'' is a 2007 platform game based on the animated television series ''The Simpsons'' made for the Nintendo DS, Wii, Xbox 360, PlayStation 2, PlayStation 3 and PlayStation Portable. The game was published, and distributed by Ele ...
'', and stars as the main antagonist in ''The Simpsons'' Ride at Universal Studios' theme parks. A lover of
Gilbert and Sullivan Gilbert and Sullivan was a Victorian-era theatrical partnership of the dramatist W. S. Gilbert (1836–1911) and the composer Arthur Sullivan (1842–1900), who jointly created fourteen comic operas between 1871 and 1896, of which '' H.M.S. Pin ...
operettas, Sideshow Bob is also known for his singing voice; several of Grammer's performances have been included in ''The Simpsons'' musical compilations.


Appearances


On ''The Simpsons''

The character of Sideshow Bob began his career as the non-speaking sidekick on
Krusty the Clown Herschel Shmoikel Pinchas Yerucham Krustofsky (; ) better known by his stage name Krusty the Clown (sometimes spelled as Krusty the Klown), is a recurring character on the animated television series ''The Simpsons''. He is voiced by Dan Caste ...
's television show. Bob first appears in "
The Telltale Head "The Telltale Head" is the eighth episode of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on February 25, 1990. It was written by Al Jean, Mike Reiss, Sam Simon and Matt Gr ...
" (
season 1 Season One may refer to: Albums * ''Season One'' (Suburban Legends album), 2004 * ''Season One'' (All Sons & Daughters album), 2012 * ''Season One'' (Saukrates album), 2012 See also * * * Season 2 (disambiguation) * Season 4 (disambigua ...
, 1990). In the episode, he and Krusty plan a big event for whoever knows information of who captured the head of Jeremiah Springfield's statue, and joins in on the town mob when it is discovered that
Bart Simpson Bartholomew JoJo "Bart" Simpson is a fictional character in the American animated television series ''The Simpsons'' and part of the Simpson family. He is voiced by Nancy Cartwright and first appeared on television in ''The Tracey Ullman Show'' ...
took it. However, after repeated instances of abuse, including being shot from a cannon and hit constantly with pies, the
Yale Yale University is a private research university in New Haven, Connecticut. Established in 1701 as the Collegiate School, it is the third-oldest institution of higher education in the United States and among the most prestigious in the worl ...
-educated Bob became angry at Krusty and resentful of the clown's success. In "
Krusty Gets Busted "Krusty Gets Busted" is the twelfth and penultimate episode of the first season of the American animated television series ''The Simpsons''. It originally aired on the Fox Network in the United States on April 29, 1990.season 1 Season One may refer to: Albums * ''Season One'' (Suburban Legends album), 2004 * ''Season One'' (All Sons & Daughters album), 2012 * ''Season One'' (Saukrates album), 2012 See also * * * Season 2 (disambiguation) * Season 4 (disambigua ...
, 1990), Bob disguised himself as Krusty and framed him for armed robbery of the
Kwik-E-Mart The Kwik-E-Mart (spelled "Quick-E-Mart" in " Bart the General") is a convenience store in the animated television series ''The Simpsons''. It is a parody of American convenience stores, such as 7-Eleven and Cumberland Farms, and depicts many of t ...
. After Krusty is arrested, Bob takes control of the show, introducing children to elements of
high culture High culture is a subculture that emphasizes and encompasses the cultural objects of aesthetic value, which a society collectively esteem as exemplary art, and the intellectual works of philosophy, history, art, and literature that a society co ...
. However, Bob's reign is short-lived; Bart exposes him as the robber, Krusty is released, and Bob is fired and sent to jail. In " Black Widower" (
season 3 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 1992), Bob's first major appearance after framing Krusty, he is released from prison and marries Bart's aunt
Selma Bouvier Patricia Maleficent "Patty" Bouvier and Selma Bouvier-Terwilliger-Hutz-McClure-Discotheque-Simpson-D'Amico () are fictional characters in the American animated sitcom ''The Simpsons''. They are identical Twin, twins and are voiced by Julie Kavne ...
as part of a scheme to inherit money she has
invested Investment is the dedication of money to purchase of an asset to attain an increase in value over a period of time. Investment requires a sacrifice of some present asset, such as time, money, or effort. In finance, the purpose of investing is ...
in the stock market. Bob attempts to blow Selma up during their
honeymoon A honeymoon is a vacation taken by newlyweds immediately after their wedding, to celebrate their marriage. Today, honeymoons are often celebrated in destinations considered exotic or romantic. In a similar context, it may also refer to the phase ...
, but Bart again foils the plan and Sideshow Bob returns to prison. After being
parole Parole (also known as provisional release or supervised release) is a form of early release of a prison inmate where the prisoner agrees to abide by certain behavioral conditions, including checking-in with their designated parole officers, or ...
d from prison in " Cape Feare" (
season 5 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 1993), Bob targets Bart directly, threatening him repeatedly and forcing the Simpsons into hiding as part of the Witness Relocation Program. Bob follows them to their hideout, a
houseboat A houseboat is a boat that has been designed or modified to be used primarily as a home. Most houseboats are not motorized as they are usually moored or kept stationary at a fixed point, and often tethered to land to provide utilities. Ho ...
on Terror Lake, and, after subduing the family, prepares to kill Bart. He allows a final request, however, and Bart asks to hear Bob sing the entire score of ''
H.M.S. Pinafore ''H.M.S. Pinafore; or, The Lass That Loved a Sailor'' is a comic opera in two acts, with music by Arthur Sullivan and a libretto by W. S. Gilbert. It opened at the Opera Comique in London, on 25 May 1878 and ran for 571 performances, which ...
''. Although Bob finishes singing and nearly kills Bart, the delaying tactic leads to Bob's third arrest as the houseboat had drifted all the way back to Springfield. Bob is released from prison once again in "
Sideshow Bob Roberts "Sideshow Bob Roberts" is the fifth episode of the sixth season of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on October 9, 1994. Kelsey Grammer returns in his fourth major ...
" (
season 6 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 1994), and runs for Mayor of Springfield as the
Republican Party Republican Party is a name used by many political parties around the world, though the term most commonly refers to the United States' Republican Party. Republican Party may also refer to: Africa * Republican Party (Liberia) *Republican Party ...
candidate. He defeats
Democratic Party Democratic Party most often refers to: *Democratic Party (United States) Democratic Party and similar terms may also refer to: Active parties Africa * Botswana Democratic Party * Democratic Party of Equatorial Guinea *Gabonese Democratic Party *De ...
incumbent
Joe Quimby Mayor Joseph Fitzgerald O'Malley Fitzpatrick O'Donnell The Edge "Joe" Quimby, nicknamed Diamond Joe, is a recurring character from the animated sitcom television series ''The Simpsons''. He is voiced by Dan Castellaneta, and first appeared in th ...
in a landslide, but Bart and Lisa discover from
Waylon Smithers Waylon Joseph Smithers Jr., usually referred to as Mr. Smithers or simply Smithers, is a recurring fictional character in the animated sitcom ''The Simpsons'', voiced by Harry Shearer. He first appeared in " Homer's Odyssey", although his voice c ...
that Bob rigged the election by using the names of deceased people. Bob is put on trial and claims himself innocent, but is tricked by Bart and Lisa to expose himself guilty, leading to another incarceration. Sideshow Bob escapes from prison for the first time in "
Sideshow Bob's Last Gleaming "Sideshow Bob's Last Gleaming" is the ninth episode of the seventh season of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on November 26, 1995. In this episode, Sideshow Bob ...
" ( season 7, 1995), and threatens to blow up Springfield with a
nuclear bomb A nuclear weapon is an explosive device that derives its destructive force from nuclear reactions, either fission (fission bomb) or a combination of fission and fusion reactions (thermonuclear bomb), producing a nuclear explosion. Both bomb ...
unless the city stops broadcasting all television shows. He is thwarted when he finds out that the bomb itself is a dud, then kidnaps Bart and flies the Wright Brothers' plane in an attempt to kill himself, Bart, and Krusty (who is hiding inside a shack, improvising a performance on the
Emergency Broadcast System The Emergency Broadcast System (EBS), sometimes called the Emergency Broadcasting System or the Emergency Action Notification System (EANS), was an emergency warning system used in the United States. It replaced the previous CONELRAD system an ...
). This too is thwarted, and Bob returns to prison. In the following season, Bob takes advantage of the prison's work release program, and appears to be genuinely redeemed. "
Brother from Another Series "Brother from Another Series" is the sixteenth episode of the eighth season of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on February 23, 1997. Sideshow Bob is released fro ...
" (
season 8 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 1997) reveals that Bob only became Krusty's sidekick after his younger brother Cecil failed an audition ten years prior, because Krusty considered Bob to be a perfect
comic foil A double act (also known as a comedy duo) is a form of comedy originating in the British music hall tradition, and American vaudeville, in which two comedians perform together as a single act. Pairings are typically long-term, in some cases fo ...
.
Reverend Lovejoy Reverend Timothy "Tim" Lovejoy, Jr. is a recurring character in the animated television series '' The Simpsons''. He is voiced by Harry Shearer, and first appeared in the episode "The Telltale Head". Rev. Lovejoy is the minister at The First ...
declares him a changed man and recommends him for a
work release In prison systems, work release programs allow a prisoner who is sufficiently trusted or can be sufficiently monitored to go outside the prison and work at a place of employment, returning to prison when their shift is complete. Some work release ...
opportunity. Bob is discharged from prison into the care of Cecil, who is now Springfield's chief hydrological and hydrodynamical engineer. However, the scheming Cecil, still smarting over his failed audition for Krusty, tries to frame Bob by
sabotaging Sabotage is a deliberate action aimed at weakening a polity, effort, or organization through subversion, obstruction, disruption, or destruction. One who engages in sabotage is a ''saboteur''. Saboteurs typically try to conceal their identitie ...
the Springfield Dam by having it burst across Springfield. Bob, Bart, and Lisa together stop Cecil and save the town, and both brothers, despite Bob's genuine innocence, are sent to prison. Bob returned in "
Day of the Jackanapes "Day of the Jackanapes" is the thirteenth episode of the twelfth season of the American animated television series ''The Simpsons''. It first aired on the Fox network in the United States on February 18, 2001. In the episode, Krusty ann ...
" ( season 12, 2001), where he discovers in prison that Krusty has erased all of the early shows featuring Sideshow Bob as Krusty himself is declaring his fifth and final retirement after being annoyed with the network executives. Bob is released from prison and develops a plot to kill Krusty using Bart as a
suicide bomber A suicide attack is any violent attack, usually entailing the attacker detonating an explosive, where the attacker has accepted their own death as a direct result of the attacking method used. Suicide attacks have occurred throughout histor ...
during Krusty's retirement special. Everything goes just as Bob had planned, and just when Bob was about to succeed in murdering both his enemies, he overhears Krusty publicly holding himself responsible for turning Bob into a criminal, expressing his regret of mistreating Bob during his years as Sideshow. To appease things, Krusty sings himself a song on Bob's behalf, and being touched by this, Bob decides to abort his plan of
attempted murder Attempted murder is a crime of attempt in various jurisdictions. Canada Section 239 of the ''Criminal Code'' makes attempted murder punishable by a maximum of life imprisonment. If a gun is used, the minimum sentence is four, five or seven ye ...
and reconciles with Krusty, although he is returned to prison for it. Bob's aid is sought by Springfield police in "
The Great Louse Detective "The Great Louse Detective" is the sixth episode of the fourteenth season of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on December 15, 2002. In the episode, the Simpson f ...
" ( season 14, 2002). After an attempt is made on
Homer Simpson Homer Jay Simpson is a fictional character and the main protagonist of the American animated sitcom ''The Simpsons''. He is voiced by Dan Castellaneta and first appeared, along with the rest of his family, in ''The Tracey Ullman Show'' short ...
's life, Bob is released from prison to help find the culprit. During the adventure, Bob is given advice to kill Bart without hesitation, instead of being tricked into delay or screwing up on his plots. When the mystery is solved (it was Frank Grimes's son), he returns to murder Bart. However, Bob finds he is "accustomed to his art'sface" and cannot do it. In "
The Italian Bob "The Italian Bob" is the eighth episode of the seventeenth season of the American animated television series ''The Simpsons''. It first aired on the Fox network in the United States on December 11, 2005. Serving as a sequel to " The Great Louse ...
" (
season 17 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2005), it is revealed that Bob had moved to Italy to make a fresh start. He was eventually elected mayor of the village of Salsiccia in
Tuscany it, Toscano (man) it, Toscana (woman) , population_note = , population_blank1_title = , population_blank1 = , demographics_type1 = Citizenship , demographics1_footnotes = , demographics1_title1 = Italian , demogra ...
and marries a local woman named
Francesca Francesca is an Italian female given name, derived from the Latin male name ''Franciscus'' meaning 'the Frenchman' It is widely used in most Romance languages, including Italian, French and Catalan, and place of origin is Italy. It is derived f ...
, with whom he has a son named Gino. The Simpson family, in Italy to retrieve a car for
Mr. Burns Charles Montgomery Plantagenet Schicklgruber "Monty" Burns, usually referred to as Mr. Burns, Monty, or C. Montgomery Burns, is a recurring character and the main antagonist of the animated television series ''The Simpsons'', voiced initially by ...
, encounters him by chance. Bob welcomes them with hospitality on the condition that they not reveal his dark felonious past; however, a drunken Lisa jokes about Bob's criminal deeds and reveals his prison uniform, alienating Bob from his citizens. Bob is angered enough to change his dream of killing Bart to killing the whole Simpson family. Upon catching up to Bob, his wife and his son swear a
vendetta Vendetta may refer to: * Feud or vendetta, a long-running argument or fight Film * ''Vendetta'' (1919 film), a film featuring Harry Liedtke * ''Vendetta'' (1950 film), an American drama produced by Howard Hughes * ''Vendetta'' (1986 film), an ...
with him on all the Simpsons. The entire Terwilliger family returns in " Funeral for a Fiend" ( season 19, 2007) in which Bob's father, Robert Terwilliger Sr., and mother, Dame Judith Underdunk, make their first appearances. Cecil also appears a second time on the show. Bob at first attempts to kill the whole family a second time, but his plan fails. Bob fakes his own death during his trial and locks Bart in the
coffin A coffin is a funerary box used for viewing or keeping a corpse, either for burial or cremation. Sometimes referred to as a casket, any box in which the dead are buried is a coffin, and while a casket was originally regarded as a box for jewe ...
, which he attempts to
cremate Cremation is a method of final disposition of a dead body through burning. Cremation may serve as a funeral or post-funeral rite and as an alternative to burial. In some countries, including India and Nepal, cremation on an open-air pyre is a ...
at the otherwise empty
funeral home A funeral home, funeral parlor or mortuary, is a business that provides burial and funeral services for the dead and their families. These services may include a prepared wake and funeral, and the provision of a chapel for the funeral. Services ...
as all the Terwilligers laugh maniacally. They are foiled by Lisa and the rest of the Simpson family and sent to prison. In "
Sex, Pies and Idiot Scrapes "Sex, Pies and Idiot Scrapes" is the first episode of the twentieth season of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on September 28, 2008. In the episode, Homer meet ...
" ( season 20, 2008), Bob is one of the wanted criminals in Homer and Ned Flanders's bounty hunter job despite already being in prison, which he escapes from at the end of the episode. In " Wedding for Disaster" ( season 20, 2009), Bart and Lisa initially suspect Bob of kidnapping Homer to prevent him from attending his second wedding with
Marge Marge is a feminine given name, a shortened form of Marjorie, Margot or Margaret. Notable Marges include: People * Marge (cartoonist) (1904–1993), pen name of Marjorie Henderson Buell, American cartoonist * Marge Anderson (1932–2013), Ojibwe ...
(due to a keychain they found had an 'S' and a 'B'), but Krusty provides him with an alibi, explaining to the kids that Bob was with him the whole day. Eventually, Bob and the kids discover the true culprits,
Patty and Selma Patricia Maleficent "Patty" Bouvier and Selma Bouvier-Terwilliger-Hutz-McClure-Discotheque-Simpson-D'Amico () are fictional characters in the American animated sitcom ''The Simpsons''. They are identical twins and are voiced by Julie Kavner who ...
. In " O Brother, Where Bart Thou?" (
season 21 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2009), Bob makes a non-speaking cameo appearance in Bart's dream sequence while the latter becomes desperate of having a younger brother. Cecil makes his third appearance in ''The Simpsons'' by appearing alongside Bob; the brothers are flying kites together. Bob reappears again in the episode "
The Bob Next Door "The Bob Next Door" is the twenty-second and penultimate episode of the twenty-first season of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on May 16, 2010. In the episode, ...
" (
season 21 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2010). He switches faces with his prison cellmate Walt Warren. Bob returns to Springfield and moves into the house next to the Simpson family, assuming Walt's identity. He exploits this to make his latest attempt to kill Bart legally over state lines, but is foiled again and gets taken away by
state police State police, provincial police or regional police are a type of sub-national territorial police force found in nations organized as federations, typically in North America, South Asia, and Oceania. These forces typically have jurisdiction o ...
. Bob appears in "
At Long Last Leave "At Long Last Leave" is the fourteenth episode of the twenty-third season of the American animated television series ''The Simpsons'', and the 500th episode overall of the series. In the episode, the Simpsons discover that the inhabitants of Spr ...
" (
season 23 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2012), the 500th episode of ''The Simpsons''. He attends a
town meeting Town meeting is a form of local government in which most or all of the members of a community are eligible to legislate policy and budgets for local government. It is a town- or city-level meeting in which decisions are made, in contrast with ...
to decide if the Simpson family should be
banished Banished may refer to: * ''Banished'' (TV series), a 2015 drama television series * ''Banished'' (film), a 2007 documentary * ''Banished'' (video game), a city-building strategy game by Shining Rock Software * Banished (Halo) The ''Halo'' vi ...
from Springfield, and is one of many who express their desire for it to happen. He makes a silent appearance in "
Moonshine River "Moonshine River" is the first episode of the twenty-fourth season of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on September 30, 2012. In the UK and Ireland, the episode ...
" (
season 24 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2012), where he runs across the train tracks trying to kill Bart, but ends up getting hit by a train. In " The Man Who Grew Too Much" (
season 25 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2014), he was revealed to be a Chief Scientist for a
genetic engineering Genetic engineering, also called genetic modification or genetic manipulation, is the modification and manipulation of an organism's genes using technology. It is a set of technologies used to change the genetic makeup of cells, including t ...
company named Monsarno, having received the position after he was selected as a test subject and published the results of the experiments to which he was subjected. He and Lisa bond over their interest in
Walt Whitman Walter Whitman (; May 31, 1819 – March 26, 1892) was an American poet, essayist and journalist. A humanist, he was a part of the transition between transcendentalism and realism, incorporating both views in his works. Whitman is among ...
, but Bob reveals that he has also genetically modified himself to give himself various
superhuman The term superhuman refers to humans or human-like beings with enhanced qualities and abilities that exceed those naturally found in humans. These qualities may be acquired through natural ability, self-actualization or technological aids. Th ...
abilities, intending to acquire DNA from the relics of various
historical figure A historical figure is a significant person in history. The significance of such figures in human progress has been debated. Some think they play a crucial role, while others say they have little impact on the broad currents of thought and socia ...
s stored in the Springfield Museum to make himself a superhuman
dictator A dictator is a political leader who possesses absolute power. A dictatorship is a state ruled by one dictator or by a small clique. The word originated as the title of a Roman dictator elected by the Roman Senate to rule the republic in time ...
. After tempted into a murderous rage, he chases down Bart and Lisa and is about to kill them but however, he is provoked into a fight and he realizes that he has become a crude monster and jumps off the Springfield Dam. The episode ends with Bob underwater in the lake, shown to have survived because the
gill A gill () is a respiratory organ that many aquatic organisms use to extract dissolved oxygen from water and to excrete carbon dioxide. The gills of some species, such as hermit crabs, have adapted to allow respiration on land provided they are ...
s he gave himself allow him to live. Bob also appears in "
Clown in the Dumps "Clown in the Dumps" is the twenty-sixth season premiere of the American animated television series ''The Simpsons'' and the 553rd episode of the series overall. It first aired in the United States on the Fox network on September 28, 2014, with t ...
" (
season 26 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2014). Having returned to prison, he offered his condolences to Krusty after the death of his father,
Rabbi Krustofsky The American animated television series ''The Simpsons'' contains a wide range of minor and supporting characters like co-workers, teachers, students, family friends, extended relatives, townspeople, local celebrities, and even animals. The write ...
. Several episodes later, Bob returned in "
Blazed and Confused "Blazed and Confused" is the seventh episode of the twenty-sixth season of the American animated television series ''The Simpsons'', and 559th episode in the series. Originally broadcast on the Fox network in the United States on November 16, 201 ...
" (
season 26 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2014), where he meets Mr. Lassen, Bart's former teacher, who was now reduced to working in prison as a
guard Guard or guards may refer to: Professional occupations * Bodyguard, who protects an individual from personal assault * Crossing guard, who stops traffic so pedestrians can cross the street * Lifeguard, who rescues people from drowning * Prison gu ...
after Bart's earlier actions at a "Blazing Guy" festival got him fired. Despite Lassen's offer to get him out, Bob rejects the idea that they team up as Lassen thought that they would take turns gutting Bart. In "
Treehouse of Horror XXVI "Treehouse of Horror XXVI" is the fifth episode of the twenty-seventh season of the American animated television series ''The Simpsons'', the 26th episode in the ''Treehouse of Horror'' series of Halloween specials, and the 579th episode of the s ...
" (
season 27 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2015), in the first segment called "Wanted: Dead, then Alive", Bob uses
Milhouse Milhouse Mussolini Van Houten is a recurring character in the Fox animated television series ''The Simpsons'' voiced by Pamela Hayden and created by Matt Groening. Milhouse is Bart Simpson's best friend in Mrs. Krabappel's fourth grade class at ...
's phone to trap Bart in the band classroom and successfully kills him. In peace with himself, Bob moves on from Bart to pursue other dreams, however, due to Bob chasing down Bart for so long, Bob finds his life so meaningless in Bart's absence that he creates a machine to bring Bart back to life so that he can keep killing his enemy over and over, until the other Simpsons find Bob's location and rescue Bart, and Bart uses the resurrection machine to turn Bob into a twisted amalgamation of creatures. Bob also appears in the episode "
Gal of Constant Sorrow "Gal of Constant Sorrow" is the fourteenth episode of the twenty-seventh season of the American animated television series ''The Simpsons'', and the 588th episode of the series overall. It aired in the United States on Fox on February 21, 2016. P ...
" (
season 27 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2016), grunting in annoyance as he wipes off Bart's
graffiti Graffiti (plural; singular ''graffiti'' or ''graffito'', the latter rarely used except in archeology) is art that is written, painted or drawn on a wall or other surface, usually without permission and within public view. Graffiti ranges from s ...
from Hettie Mae Boggs' promo poster on the wall along with
Snake Jailbird The American animated television series ''The Simpsons'' contains a wide range of minor and supporting characters like co-workers, teachers, students, family friends, extended relatives, townspeople, local celebrities, and even animals. The writ ...
and other inmates. Bob returns in " Treehouse of Horror XXVII" (
season 28 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2016), the 600th episode of ''The Simpsons''. In the opening sequence, he is the self-appointed leader of a four-member group consisting of Homer's enemies, including Bob himself and the ghost of Frank Grimes. Wanting revenge once more, the group attempts to kill the Simpsons but is ultimately killed by
Maggie Maggie is a common short form of the name Magdalena, Magnolia, Margaret. Maggie may refer to: People Women * Maggie Adamson, Scottish musician * Maggie Aderin-Pocock (born 1968), British scientist * Maggie Alderson (born 1959), A ...
, except Grimes's ghost. In the ending sequence, Bob is one of the characters featured in the "600" song played by
Judith Owen Judith Owen (born 2 January 1969) is a Welsh singer-songwriter. Her first North American album, ''Emotions on a Postcard'', was released in 1996 and has been followed by several additional albums. She is co-founder of Twanky Records with her hu ...
. In "
Havana Wild Weekend "Havana Wild Weekend" is the seventh episode of the twenty-eighth season of the American animated television series ''The Simpsons'', and the 603rd episode of the series overall. The episode was directed by Bob Anderson and written by Deb Lacust ...
" (
season 28 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2016), Sideshow Bob appeared in the backgrounds at the Cuba's check-in. Bob also makes a non-speaking cameo appearance in "
The Nightmare After Krustmas "The Nightmare After Krustmas" is the tenth episode of the twenty-eighth season of the American animated television series ''The Simpsons'', and the 606th episode of the series overall. It aired in the United States on Fox on December 11, 2016. P ...
" (
season 28 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2016); he is amongst the crowd witnessing Krusty nearly drowning in a frozen lake while holding up a sign saying "Die Clown". He's had a major appearance in " Gone Boy" (
season 29 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
, 2017), when he tries to track down the whereabouts of Bart after he goes missing and is presumed dead. Bob finds Bart and proceeds to kill him and
Milhouse Milhouse Mussolini Van Houten is a recurring character in the Fox animated television series ''The Simpsons'' voiced by Pamela Hayden and created by Matt Groening. Milhouse is Bart Simpson's best friend in Mrs. Krabappel's fourth grade class at ...
, but saves them at the last minute due to the influence of the prison therapist's lessons of potentially moving on from wanting to kill Bart. The epilogue features an older Bob, now known as Elder Bob, being an lighthouse keeper and still having regrets of not killing Bart. In "
The Fat Blue Line "The Fat Blue Line" is the third episode of the thirty-first season of the American animated television series ''The Simpsons'', and the 665th episode overall. It aired in the United States on Fox on October 13, 2019. The writer was Bill Odenkirk. ...
" ( season 31, 2019), Bob escapes from prison once again, only to be hit by a rake truck. Several episodes later, in " Bobby, It's Cold Outside" ( season 31, 2019), he is hired to play Santa Claus at a theme park, and later helps the Simpsons discover who is stealing everyone's Christmas gifts. Bob returned in a non-speaking cameo in "
Meat Is Murder ''Meat Is Murder'' is the second studio album by English rock band the Smiths, released on 11 February 1985 by Rough Trade Records. It became the band's only studio album to reach number one on the UK Albums Chart, and stayed on the chart for ...
" ( season 33, 2022), where he is seen signing the chests of citizens like Milhouse's father
Kirk Van Houten The American animated television series ''The Simpsons'' contains a wide range of minor and supporting characters like co-workers, teachers, students, family friends, extended relatives, townspeople, local celebrities, and even animals. The writ ...
at the celebration of
Krusty Burger Springfield is the primary fictional setting of the American animated sitcom ''The Simpsons'' and related media. It is an average-sized, fictional city within an indeterminate state in the United States. The fictional city's geography, surroun ...
's 50th anniversary, a callback to the "Die Bart, Die" scene from "Cape Feare".


Other media

In addition to regular roles in the television series, Sideshow Bob has made several appearances in other ''Simpsons'' media. Kelsey Grammer recorded several Sideshow Bob lines for ''
The Simpsons Movie ''The Simpsons Movie'' is a 2007 American animated comedy film based on the long-running animated sitcom ''The Simpsons''. The film was directed by the show's supervising director David Silverman and stars the show's regular cast of Dan Caste ...
,'' but the scene was cut. Sideshow Bob has made regular appearances in the monthly ''Simpsons Comics'', and several of Kelsey Grammer's singing performances have been included in ''The Simpsons'' CD compilations. His performance of the ''
H.M.S. Pinafore ''H.M.S. Pinafore; or, The Lass That Loved a Sailor'' is a comic opera in two acts, with music by Arthur Sullivan and a libretto by W. S. Gilbert. It opened at the Opera Comique in London, on 25 May 1878 and ran for 571 performances, which ...
'' in "Cape Feare" was later included on the album ''
Go Simpsonic with The Simpsons ''Go Simpsonic with The Simpsons'' is the 1999 soundtrack album from ''The Simpsons''. It takes many of the musical numbers from the series which were either not included in the previous album, '' Songs in the Key of Springfield'', or were creat ...
,'' and the song " The Very Reason That I Live" from "The Great Louse Detective" was included on '' The Simpsons: Testify''. A previously unaired song, "Hullaba Lula", originally written for "Day of the Jackanapes", was also included on that compilation. The producers modeled the song after "
Zip-a-Dee-Doo-Dah "Zip-a-Dee-Doo-Dah" is a song composed by Allie Wrubel with lyrics by Ray Gilbert for the Disney 1946 live action and animated movie ''Song of the South'', sung by James Baskett. For "Zip-a-Dee-Doo-Dah", the film won the Academy Award for Best Or ...
", but were forced to remove the song from the episode when they were unable to obtain the rights to it. In ''
The Simpsons Game ''The Simpsons Game'' is a 2007 platform game based on the animated television series ''The Simpsons'' made for the Nintendo DS, Wii, Xbox 360, PlayStation 2, PlayStation 3 and PlayStation Portable. The game was published, and distributed by Ele ...
'', released in November 2007, Bob has a speaking
cameo appearance A cameo role, also called a cameo appearance and often shortened to just cameo (), is a brief appearance of a well-known person in a work of the performing arts. These roles are generally small, many of them non-speaking ones, and are commonly eit ...
at the end of the chapter titled "Invasion of the Yokel-Snatchers" in which he was working with
Kang and Kodos Kang and Kodos Johnson are a duo of fictional recurring characters in the animated television series ''The Simpsons''. Kang is voiced by Harry Shearer and Kodos by Dan Castellaneta. They are green, perpetually drooling, octopus-like aliens fro ...
. Sideshow Bob appears in the 1991 ''
The Simpsons Arcade Game ''The Simpsons'' is an arcade beat 'em up developed and published by Konami released in 1991. It was the first video game based on the ''Simpsons'' franchise to be released in North America. The game allows up to four players to control memb ...
'', on the fifth level where he is pulling a cart containing a roast chicken health pick up. Bob was also included as a level boss in the 1991 video game '' Bart vs. the Space Mutants''. Sideshow Bob plays a lead role in The Simpsons Ride, which opened at
Universal Studios Florida Universal Studios Florida (also known as Universal Studios or USF) is a theme park located in Orlando, Florida. Primarily themed to movies, television and other aspects of the entertainment industry, the park opened to the public on June 7, 1990 ...
and
Universal Studios Hollywood Universal Studios Hollywood is a film studio and theme park in the San Fernando Valley area of Los Angeles County, California. About 70% of the studio lies within the unincorporated county island known as Universal City while the rest lies wit ...
in May 2008. Voiced by Grammer, he is the main villain in the ride, having escaped from prison to get revenge on the Simpson family. In '' The Simpsons: Tapped Out'', a
city-building game A city-building game, or town-building game, is a genre of simulation video game where players act as the overall planner and leader of a city or town, looking down on it from above, and being responsible for its growth and management strategy. ...
released in February 2012, Sideshow Bob occurs as a bonus. Popping up every couple hours, the players are given a chance to tap on him to receive a small sum of money, and "send" him to jail. In a later update to the game, Sideshow Bob also has a stand in Krusty Land, where players get to pop balloons for a chance to win donuts and Krusty
tickets Ticket or tickets may refer to: Slips of paper * Lottery ticket * Parking ticket, a ticket confirming that the parking fee was paid (and the time of the parking start) * Toll ticket, a slip of paper used to indicate where vehicles entered a to ...
. The Simpsons: Tapped Out Terwilligers content update was released April 14, 2015 and has several references to the Simpsons episodes with Sideshow Bob. This game event was split in 3 acts and ended June 4, 2015. New characters, skins and costumes include Sideshow Bob, Cecil Terwilliger, Gino Terwilliger, Francesca Terwilliger, Dr. Robert Terwilliger Sr., Judith Underdunk, Captain Bob, and Opera Krusty. Most of the event action takes place at Monsarno Research and Opera House.


Character


Creation

Sideshow Bob first appeared in "
The Telltale Head "The Telltale Head" is the eighth episode of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on February 25, 1990. It was written by Al Jean, Mike Reiss, Sam Simon and Matt Gr ...
", the eighth episode of season one. His design was relatively simple compared to later incarnations, and his hairstyle was rounded. However, towards the end of the episode, he appears again, in a panning shot of a crowd, with his familiar hairstyle. His second appearance, and first major one, was in season one's twelfth episode "
Krusty Gets Busted "Krusty Gets Busted" is the twelfth and penultimate episode of the first season of the American animated television series ''The Simpsons''. It originally aired on the Fox Network in the United States on April 29, 1990.Jay Kogen Jay Kogen is an American comedy writer, producer, actor and director. Biography He was born to a Jewish family. His father is comedy writer Arnie Kogen. In 2001, Kogen had a son, Charlie, who is now a musician. Career Kogen co-wrote several e ...
and
Wallace Wolodarsky Wallace Wolodarsky, also billed as Wally Wolodarsky, is an American actor, screenwriter, television producer, and film director known for being one of the writers for ''The Simpsons'' during the first four seasons with his writing partner Jay K ...
. Bob's design was updated for "Krusty Gets Busted"; as the episode's animation style evolved, director
Brad Bird Phillip Bradley Bird (born September 24, 1957) is an American film director, animator, screenwriter, producer, and voice actor. He has had a career spanning forty years in both animation and live-action. Bird was born in Montana and grew up in ...
made the character of Sideshow Bob sleeker and more refined, to fit Grammer's voice technique. Following the re-design, animators tried to redraw his scenes in "The Telltale Head", but had insufficient time before the show was produced.Moore, Rich. (2001). Commentary for "The Telltale Head", in ''The Simpsons: The Complete First Season'' VD 20th Century Fox. Bob has no lines of dialogue during the first half of "Krusty Gets Busted"; the character's only communication takes the form of a
slide whistle A slide whistle (variously known as a swanee or swannee whistle, lotos flute piston flute, or jazz flute) is a wind instrument consisting of a fipple like a recorder's and a tube with a piston in it. Thus it has an air reed like some woodwind ...
. This was designed to make Bob appear simplistic, so that when he finally spoke, viewers would be surprised to hear his sophisticated vocabulary.Jean, Al. (2001). Commentary for "Krusty Gets Busted", in ''The Simpsons: The Complete First Season'' VD 20th Century Fox. An early version of the script for "Krusty Gets Busted" called for
James Earl Jones James Earl Jones (born January 17, 1931) is an American actor. He has been described as "one of America's most distinguished and versatile" actors for his performances in film, television, and theater, and "one of the greatest actors in America ...
to voice Bob, but the producers instead selected
Kelsey Grammer Allen Kelsey Grammer (born February 21, 1955) is an American actor and producer. He gained notoriety and acclaim for his role as psychiatrist Dr. Frasier Crane on the NBC sitcom ''Cheers'' (1984-1993) and its spin-off ''Frasier'' (1993-2004), f ...
.Bird, Brad. (2001). Commentary for "Krusty Gets Busted", in ''The Simpsons: The Complete First Season'' VD 20th Century Fox. For Bob's voice, Grammer performed an impression of theatre
actor An actor or actress is a person who portrays a character in a performance. The actor performs "in the flesh" in the traditional medium of the theatre or in modern media such as film, radio, and television. The analogous Greek term is (), lit ...
and director
Ellis Rabb Ellis W. Rabb (June 20, 1930 – January 11, 1998) was an American actor and director who in 1959 formed the Association of Producing Artists, a theatre company that brought new works and noteworthy revivals to Broadway and to regional theatres. ...
. Grammer had once worked for Rabb, whose "lamenting tones became hefoundation for Sideshow Bob".Grammer, Kelsey. (2006). Commentary for "Brother From Another Series", in ''The Simpsons: The Complete Eighth Season'' VD 20th Century Fox. Sideshow Bob's full name is Robert Underdunk Terwilliger. His
last name In some cultures, a surname, family name, or last name is the portion of one's personal name that indicates one's family, tribe or community. Practices vary by culture. The family name may be placed at either the start of a person's full name, ...
was first revealed in "Black Widower" while his
middle name In various cultures, a middle name is a portion of a personal name that is written between the person's first given name and their surname. A middle name is often abbreviated and is then called middle initial or just initial. A person may be ...
was first revealed in "Sideshow Bob Roberts". Competing theories as to the origin of his name exist; some sources say he was named after the character Dr. Terwilliker, a megalomaniac outwitted by a boy named Bart in the film ''
The 5,000 Fingers of Dr. T ''The 5,000 Fingers of Dr. T.'' is a 1953 American musical fantasy film about a boy who dreams himself into a fantasy world ruled by a diabolical piano teacher enslaving children to practice piano forever. It was the only feature film written by ...
'' by Dr. Seuss, but others say he was named after
Terwilliger Boulevard Terwilliger Boulevard is a street in Portland, Oregon, U.S. It begins at SW 6th Avenue and SW Sheridan Street south of Portland State University. It passes through the neighborhoods of Marquam Hill, Southwest Hills, and Burlingame and by Lewis ...
in
Portland, Oregon Portland (, ) is a port city in the Pacific Northwest and the largest city in the U.S. state of Oregon. Situated at the confluence of the Willamette and Columbia rivers, Portland is the county seat of Multnomah County, the most populous co ...
. Yet another theory is that he was named after Sergeant Terwilliger and Mrs. Underdunk in the pilot episode of the TV show ''
Hunter Hunting is the human activity, human practice of seeking, pursuing, capturing, or killing wildlife or feral animals. The most common reasons for humans to hunt are to harvest food (i.e. meat) and useful animal products (fur/hide (skin), hide, ...
''.


Development

For season three's " Black Widower", the writers echoed the premise of Wile E. Coyote chasing the Road Runner from
Looney Tunes ''Looney Tunes'' is an American animated comedy short film series produced by Warner Bros. starting from 1930 to 1969, concurrently with its partner series ''Merrie Melodies'', during the golden age of American animation.
cartoons by having Bob unexpectedly insert himself into Bart's life and attempt to kill him. Executive producer
Al Jean Alfred Ernest Jean III (born January 9, 1961) is an American screenwriter and producer. Jean is well known for his work on ''The Simpsons''. He was raised near Detroit, Michigan, and graduated from Harvard University in 1981. Jean began his wri ...
has compared Bob's character to that of Wile E. Coyote, noting that both are intelligent, yet always foiled by what they perceive as an inferior intellect.Jean, Al. (2003). Commentary for "Black Widower", in ''The Simpsons: The Complete Third Season'' VD 20th Century Fox. For "Black Widower", director David Silverman updated the character model to reflect the animation of director Brad Bird.Silverman, David. (2003). Commentary for "Black Widower", in ''The Simpsons: The Complete Third Season'' VD 20th Century Fox. A rule for earlier episodes featuring Bob called for a recap of his evil deeds; this was dropped after season eight's "
Brother from Another Series "Brother from Another Series" is the sixteenth episode of the eighth season of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on February 23, 1997. Sideshow Bob is released fro ...
" when the chronology became too lengthy.Weinstein, Josh. (2006). Commentary for "Brother From Another Series", in ''The Simpsons: The Complete First Season'' VD 20th Century Fox. Another rule established by the show's writers mandated Bob's return to prison at the end of each episode, although this pattern was abandoned in later episodes like "The Great Louse Detective" and "The Italian Bob".
Bill Oakley William Lloyd Oakley (born February 27, 1966) is an American television writer and producer, known for his work on the animated comedy series ''The Simpsons''. Oakley and Josh Weinstein became best friends and writing partners at St. Albans Sc ...
and
Josh Weinstein Josh Weinstein (born May 5, 1966) is an American television writer and producer, known for his work on the animated comedy series ''The Simpsons''. Weinstein and Bill Oakley became best friends and writing partners at St. Albans School; Weins ...
, the
showrunner A showrunner (or colloquially a helmer) is the top-level executive producer of a television series production who has creative and management authority through combining the responsibilities of employer and, in comedy or dramas, typically also the ...
s for the seventh and eighth seasons, believed that every season of the show should contain an episode starring Sideshow Bob. However, by the seventh season, Bob had already been the focus of four episodes, and writers were having trouble developing new ways to include him. Weinstein describes Bob's dialogue as difficult to write, due to his unique and refined style of speaking. Despite these challenges, however, creators of ''The Simpsons'' usually look forward to "Sideshow Bob episodes"; the writers consider them enjoyable to write,Keeler, Ken. (2006). Commentary for "Brother From Another Series", in ''The Simpsons: The Complete Eighth Season'' VD 20th Century Fox. and former director
Dominic Polcino Dominic Polcino is an animation director who has worked on ''The Simpsons'', '' Mission Hill'', ''King of the Hill'', and ''Family Guy''. Polcino worked on the first season of ''Family Guy'', then left to direct for ''King of the Hill'' and then ...
describes them as "a treat" to work on.Polcino, Dominic. (2005). Commentary for "Sideshow Bob's Last Gleaming", in ''The Simpsons: The Complete Seventh Season'' VD 20th Century Fox. In "Black Widower", Sideshow Bob notes that he is a "life-long Republican". Kelsey Grammer initially expected Sideshow Bob to be a one-time role, and calls him "the most popular character I've ever played". Grammer usually joins the show's "table readings" (wherein cast members read each script together for the first time),Jean, Al. (2004). Commentary for "Cape Feare", in ''The Simpsons: The Complete Fourth Season'' VD 20th Century Fox. and former executive producer
David Mirkin David Mirkin (born ) is an American feature film and television director, writer and producer. Mirkin grew up in Philadelphia and intended to become an electrical engineer, but abandoned this career path in favor of studying film at Loyola Mar ...
described working with Grammer as very pleasant, due to his lively sense of humor. Grammer, Mirkin says, is capable of perfect readings, but noted that the actor dislikes performing Sideshow Bob's evil laugh.Mirkin, David. (2005). Commentary for "Sideshow Bob Roberts", in ''The Simpsons: The Complete Sixth Season'' VD 20th Century Fox. In a 2007 interview, ''Simpsons'' executive producer
Al Jean Alfred Ernest Jean III (born January 9, 1961) is an American screenwriter and producer. Jean is well known for his work on ''The Simpsons''. He was raised near Detroit, Michigan, and graduated from Harvard University in 1981. Jean began his wri ...
listed Grammer as one of his favorite guest stars (second only to
Phil Hartman Philip Edward Hartman (; September 24, 1948 – May 28, 1998) was a Canadian-American actor, comedian, screenwriter and graphic designer. Hartman was born in Brantford, Ontario, Canada, and his family moved to the United States w ...
), saying "his voice is so rich." Writer
George Meyer George Meyer (born 1956) is an American producer and writer. Meyer is best known for his work on ''The Simpsons'', where he led the group script rewrite sessions. He has been publicly credited with "thoroughly shap ng... the comedic sensibility ...
commented that "writing for Kelsey is great, he can give the kind of purple, florid, melodramatic speeches that most of the characters would never give. And he can sing." The show's writers admire Grammer's singing voice, and try to include a song for each appearance.
Alf Clausen Alf Heiberg Clausen (born March 28, 1941) is an American film and television composer. He is best known for his work scoring many episodes of ''The Simpsons'', for which he was the sole composer between 1990 and 2017. Clausen has scored or or ...
, the primary composer for ''The Simpsons'', commented that "
rammer A ramrod (or scouring stick) is a metal or wooden device used with muzzleloading firearms to push the projectile up against the propellant (mainly blackpowder). The ramrod was used with weapons such as muskets and cannons and was usually held ...
is so great. He's just amazing. You can tell he has this love of musical theater and he has the vocal instrument to go with it, so I know whatever I write is going to be sung the way I've heard it." Clausen composed Sideshow Bob's theme, which is played whenever Bob gets out of prison or is about to commit a sinister action, and was first used in " Cape Feare". It is based on the score of the film '' Cape Fear'', composed by
Bernard Herrmann Bernard Herrmann (born Maximillian Herman; June 29, 1911December 24, 1975) was an American composer and conductor best known for his work in composing for films. As a conductor, he championed the music of lesser-known composers. He is widely r ...
. The musical score for "Cape Feare" earned Clausen an
Emmy Award The Emmy Awards, or Emmys, are an extensive range of awards for artistic and technical merit for the American and international television industry. A number of annual Emmy Award ceremonies are held throughout the calendar year, each with the ...
nomination for Outstanding Dramatic Underscore – Series in 1994. Bob's prisoner number is often 24601, which is
Jean Valjean Jean Valjean () is the protagonist of Victor Hugo's 1862 novel ''Les Misérables''. The story depicts the character's struggle to lead a normal life and redeem himself after serving a 19-year-long prison sentence for stealing bread to feed his ...
's prisoner number in ''
Les Misérables ''Les Misérables'' ( , ) is a French historical novel by Victor Hugo, first published in 1862, that is considered one of the greatest novels of the 19th century. In the English-speaking world, the novel is usually referred to by its origina ...
''.Reiss, Mike. (2003). Commentary for "Black Widower", in ''The Simpsons: The Complete Third Season'' VD 20th Century Fox. Another trademark for Bob is a visual gag of stepping on a rake and being struck in the face with its handle; this joke first appeared in "Cape Feare". To fill time, the writers added nine consecutive iterations of the same joke in quick succession. The sequence has become known as the "rake joke" and was described by ''Entertainment Weekly'' as showing "genius in its repetitive stupidity."


Family

The episode "
Brother from Another Series "Brother from Another Series" is the sixteenth episode of the eighth season of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on February 23, 1997. Sideshow Bob is released fro ...
" introduces Bob's brother Cecil. After writer
Ken Keeler Ken Keeler is an American television producer and writer. He has written for numerous television series, most notably ''The Simpsons'' and ''Futurama''. According to an interview with David X. Cohen, he proved a theorem that appears in the ''Fut ...
was assigned to write an episode featuring Sideshow Bob, he drew inspiration from episodes of ''
Frasier ''Frasier'' () is an American television sitcom that was broadcast on NBC for 11 seasons. It premiered on September 16, 1993, and ended on May 13, 2004. The program was created and produced by David Angell, Peter Casey, and David Lee (as Grub ...
''. He decided to incorporate elements of Grammer's other show into the character of Sideshow Bob, and designed Cecil to resemble Grammer's brother on ''Frasier''. Cecil is voiced by
David Hyde Pierce David Hyde Pierce (born April 3, 1959) is an American actor and director of stage, film and television. He starred as psychiatrist Dr. Niles Crane on the NBC sitcom ''Frasier'' from 1993 to 2004, and won four Primetime Emmy Awards and a Screen ...
, who portrayed
Frasier Crane Dr. Frasier Winslow Crane (born ) is a fictional character who is both a supporting character on the American television sitcom ''Cheers'' and the titular protagonist of its spin-off ''Frasier'', portrayed by Kelsey Grammer. The character debu ...
's brother Niles. Pierce commented, "Normally, I would not do something like this. But how often do you get a chance to work with an actor like Kelsey Grammer and, more importantly, play his brother?" Several of ''Frasier'' producers were asked to review the original script and provide feedback. Their comments were positive; they only expressed concern with a very brief scene in which Cecil talks to a visible character whom he refers to as "Maris". In ''Frasier'',
Maris Crane The main character of the American television sitcom ''Frasier'' is Frasier Crane. Other regular characters include: his father Martin, brother Niles, producer Roz Doyle, and his live-in caregiver Daphne Moon. Other minor characters made regula ...
is an
unseen character An unseen character in theatre, comics, film, or television, or silent character in radio or literature, is a character that is mentioned but not directly known to the audience, but who advances the action of the plot in a significant way, and wh ...
, and the producers of ''Frasier'' asked that the scene be removed. Many of the interactions between Bob and Cecil were based on those of Niles and Frasier. Cecil was drawn to resemble
David Hyde Pierce David Hyde Pierce (born April 3, 1959) is an American actor and director of stage, film and television. He starred as psychiatrist Dr. Niles Crane on the NBC sitcom ''Frasier'' from 1993 to 2004, and won four Primetime Emmy Awards and a Screen ...
, while retaining a visual similarity to Sideshow Bob. According to director
Pete Michels Pete Michels is an American animation director who is the supervising director of ''Future-Worm!'' on Disney XD. Prior, he was a supervising director on seasons 1 and 2 of ''Rick and Morty'', an animation and supervising director on ''Family Guy' ...
, it was difficult to draw Bob and Cecil standing together, because of their comically oversized feet.Michels, Pete. (2006). Commentary for "Brother From Another Series", in ''The Simpsons: The Complete Eighth Season'' VD 20th Century Fox. Cecil returns in season 19's " Funeral for a Fiend", which introduces the brothers' previously unseen father, Dr. Robert Terwilliger, played by
John Mahoney Charles John Mahoney (June 20, 1940 – February 4, 2018) was an English-born American actor. He was known for playing Martin Crane on the NBC sitcom ''Frasier'' (1993–2004), and won a Screen Actors Guild Award for the role in 2000. Mahoney ...
. Mahoney portrayed
Martin Crane Martin Crane (born ) is a fictional character from the American television show ''Frasier'', and was played by actor John Mahoney. An army veteran and retired police detective, he is the father of Frasier and Niles Crane. Biography Although M ...
, the father of Grammer's and Pierce's characters in ''Frasier''. Whereas in ''Frasier'', Mahoney played the "down-to-Earth, average guy" to Grammer's and Hyde Pierce's "uppity snobs", Robert Terwilliger Sr. was portrayed as equally highbrow as Bob. His wife, Bob's mother, is Dame Judith Underdunk, "the finest classical actress of her generation." She sports the same curly spiked hair as her two sons. Bob also has a wife named Francesca (voiced by
Maria Grazia Cucinotta Maria Grazia Cucinotta (; born 27 July 1968) is an Italian actress who has featured in films and television series since 1990. She has also worked as a film producer, screenwriter and model. Internationally she is best known for her roles in ...
) and a son named Gino, both of whom were introduced in
season 17 A season is a division of the year based on changes in weather, ecology, and the number of daylight hours in a given region. On Earth, seasons are the result of the axial parallelism of Earth's tilted orbit around the Sun. In temperate and pola ...
episode "
The Italian Bob "The Italian Bob" is the eighth episode of the seventeenth season of the American animated television series ''The Simpsons''. It first aired on the Fox network in the United States on December 11, 2005. Serving as a sequel to " The Great Louse ...
" and returned for " Funeral for a Fiend".


Reception

The character of Sideshow Bob and Grammer's voicework have received many accolades. In 2006,
IGN ''IGN'' (formerly ''Imagine Games Network'') is an American video game and entertainment media website operated by IGN Entertainment Inc., a subsidiary of Ziff Davis, Inc. The company's headquarters is located in San Francisco's SoMa dist ...
listed him as the second-best "peripheral character" on ''The Simpsons'', commenting that Bob is "a man of contradictions; his goofy appearance, complete with palm tree like hair, doesn't seem to match up to the well spoken and even musically talented maniac." Also that year, '' Wizard'' magazine rated Bob as the 66th-greatest villain of all time. Adam Finley of
TV Squad Weblogs, Inc. was a blog network that published content on a variety of subjects, including tech news, video games, automobiles and pop culture. At one point, the network had as many as 90 blogs, although the vast majority of its traffic could be ...
wrote that "that baritone voice, the Shakespearean delivery, and the ability to go from calm and collected to stark raving mad all within the same second make Sideshow Bob one of the best recurring characters on the show." Kelsey Grammer has consistently received praise for his voicework, and has been described as "brilliant", "inimitable" and "a feast of mid-Atlantic anglophilia". In 2006, Grammer won the
Primetime Emmy Award The Primetime Emmy Awards, or Primetime Emmys, are part of the extensive range of Emmy Awards for artistic and technical merit for the American television industry. Bestowed by the Academy of Television Arts & Sciences (ATAS), the Primetime ...
for Outstanding Voice-Over Performance for his role in "
The Italian Bob "The Italian Bob" is the eighth episode of the seventeenth season of the American animated television series ''The Simpsons''. It first aired on the Fox network in the United States on December 11, 2005. Serving as a sequel to " The Great Louse ...
"; he had previously won four awards in the Outstanding Lead Actor in a Comedy Series category for his portrayal of the title role on ''Frasier''. In 2008, Grammer was included in ''
Entertainment Weekly ''Entertainment Weekly'' (sometimes abbreviated as ''EW'') is an American digital-only entertainment magazine based in New York City, published by Dotdash Meredith, that covers film, television, music, Broadway theatre, books, and popular cultu ...
''s list of the sixteen best ''Simpsons'' guest stars; Hyde Pierce was also included in that list. Ken Tucker of ''Entertainment Weekly'' wrote that "Kelsey Grammer's grand voice-performance as Sideshow Bob is Frasier pickled in arsenic." In her book '' My Life as a 10-Year-Old Boy'',
Nancy Cartwright Nancy Cartwright (born October 25, 1957) is an American actress. She is the long-time voice of Bart Simpson on the animated television series ''The Simpsons'', for which she has received a Primetime Emmy Award for Outstanding Voice-Over Perform ...
(who performs the voice of Bart Simpson) wrote that "Kelsey Grammer scores big-time by injecting caustic, bitter, contemptuous and deliciously vile energy into his rendition of Sideshow Bob. Springfield just wouldn't be the same without him." Most of the episodes featuring Bob have been well received by fans and critics. " Cape Feare" is generally regarded as one of the best episodes of ''The Simpsons''Groening, Matt. (2004). Commentary for "Cape Feare", in ''The Simpsons: The Complete Fifth Season'' VD 20th Century Fox. and placed third on ''Entertainment Weekly''s 2003 list of the show's top 25 episodes. IGN considers it the best episode of the fifth season. In 2007, '' Vanity Fair'' called it the show's fourth-best episode, because of its "masterful integration of filmic parody and a recurring character".
Ben Rayner Ben Rayner is a music critic and writer for the ''Toronto Star'' since 1998. His commentary on artists is extensively cited across the industry. Indie88 considers him "of the most respected industry professionals around." In 2012, he served on t ...
of the ''
Toronto Star The ''Toronto Star'' is a Canadian English-language broadsheet daily newspaper. The newspaper is the country's largest daily newspaper by circulation. It is owned by Toronto Star Newspapers Limited, a subsidiary of Torstar Corporation and pa ...
'' listed "Cape Feare", "Sideshow Bob's Last Gleaming" and "Brother From Another Series" among the best episodes of the series, writing "forget ''Frasier'', these are Kelsey Grammer's best roles." "
The Italian Bob "The Italian Bob" is the eighth episode of the seventeenth season of the American animated television series ''The Simpsons''. It first aired on the Fox network in the United States on December 11, 2005. Serving as a sequel to " The Great Louse ...
" and its writer
John Frink John Frink (born May 5, 1959) is an American television writer and producer. He has written several episodes of the American animated sitcom ''The Simpsons'', many of which he co-wrote with his former writing partner Don Payne. Frink and Payne ...
won a
Writers Guild of America Award The Writers Guild of America Awards is an award for film, television, and radio writing including both fiction and non-fiction categories given by the Writers Guild of America, East and Writers Guild of America West since 1949. Eligibility T ...
in 2007 in the animation category. In December 2009, Robert Canning of IGN ranked the ten episodes to feature Bob that had aired at the time. The first five Bob episodes took up the top five, with "Cape Feare" being ranked first. "The Italian Bob" was ranked tenth, with the explanation that "All the things we love about a Sideshow Bob episode—the vengeance, the familiar settings and characters, the elaborate scheming—were missing from this half-hour. Without it, Bob wasn't nearly as entertaining, and the episode didn't result in a whole lot of laughs." He noted that only "The Italian Bob" and the ninth ranked "Funeral for a Fiend" were "the only ones I'd consider clunkers. The remaining episodes are all quite fun." The character's line in "
Sideshow Bob Roberts "Sideshow Bob Roberts" is the fifth episode of the sixth season of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on October 9, 1994. Kelsey Grammer returns in his fourth major ...
", "Attempted murder? Now honestly, what is that? Do they give a Nobel prize for attempted chemistry?", briefly became an
Internet meme An Internet meme, commonly known simply as a meme ( ), is an idea, behavior, style, or image that is spread via the Internet, often through social media platforms. What is considered a meme may vary across different communities on the Internet ...
after a similar defense of President
Donald Trump Donald John Trump (born June 14, 1946) is an American politician, media personality, and businessman who served as the 45th president of the United States from 2017 to 2021. Trump graduated from the Wharton School of the University of P ...
was repeated after the Trump–Ukraine scandal.


Analysis

In ''
Planet Simpson ''Planet Simpson: How a Cartoon Masterpiece Documented an Era and Defined a Generation'', also abbreviated to ''Planet Simpson: How a Cartoon Masterpiece Defined a Generation'', is a non-fiction book about ''The Simpsons'', written by Chris Turner ...
'', author Chris Turner writes that Bob is built into a highbrow snob and conservative Republican so that the writers can continually use him as a strawman and pincushion. He represents
high culture High culture is a subculture that emphasizes and encompasses the cultural objects of aesthetic value, which a society collectively esteem as exemplary art, and the intellectual works of philosophy, history, art, and literature that a society co ...
while Krusty represents
low culture In sociology, the term Low culture identifies the forms of popular culture that have mass appeal, which is in contrast to High culture, which has a limited appeal to a smaller proportion of the populace. Culture theory proposes that both high ...
, and Bart, stuck in between, always wins out. In the book '' Leaving Springfield'', David L. G. Arnold comments that Bart is a product of a "mass-culture upbringing" and thus is Bob's enemy. Frustrated by his early role as the target of "Krusty's cheap gags", Bob frames Krusty and takes over the show. He changes the content of that show to present readings of classic literature and segments examining the emotional lives of pre-teens. He believes that by exposing the kids to high culture he will improve their lives. Arnold writes that "Bob's own conscience and morality are clearly unaffected by the high culture he represents." He also tries to "manipulate the tastes of the masses" by becoming a criminal mastermind.
Arnold Arnold may refer to: People * Arnold (given name), a masculine given name * Arnold (surname), a German and English surname Places Australia * Arnold, Victoria, a small town in the Australian state of Victoria Canada * Arnold, Nova Scotia U ...
, pp. 12–13.
Arnold believes that this is most apparent in "
Sideshow Bob Roberts "Sideshow Bob Roberts" is the fifth episode of the sixth season of the American animated television series ''The Simpsons''. It originally aired on the Fox network in the United States on October 9, 1994. Kelsey Grammer returns in his fourth major ...
", wherein he rigs the election to become the mayor of Springfield. When accused of election fraud, he rants, "Your guilty consciences may force you to vote Democratic, but secretly you yearn for a cold-hearted Republican who'll cut taxes, brutalize criminals, and rule you like a king! You need me, Springfield!" He considers himself a member of the social elite, and happily uses Machiavellian methods to acquire and maintain power.
Arnold Arnold may refer to: People * Arnold (given name), a masculine given name * Arnold (surname), a German and English surname Places Australia * Arnold, Victoria, a small town in the Australian state of Victoria Canada * Arnold, Nova Scotia U ...
, p. 17.
Bob's intelligence serves him in many ways. During the episode "Cape Feare", for example, the parole board asks Bob why he has a tattoo that says "Die, Bart, Die". Bob replies that it is German for "The, Bart, The"; members of the board are impressed by his reasoning. Believing that "nobody who speaks German could be an evil man", they release him. However, his love of high culture is sometimes used against him. In the same episode, Bob agrees to perform the operetta ''
H.M.S. Pinafore ''H.M.S. Pinafore; or, The Lass That Loved a Sailor'' is a comic opera in two acts, with music by Arthur Sullivan and a libretto by W. S. Gilbert. It opened at the Opera Comique in London, on 25 May 1878 and ran for 571 performances, which ...
'' in its entirety as a last request for Bart. The tactic stalls Bob long enough for the police to arrest him.
Arnold Arnold may refer to: People * Arnold (given name), a masculine given name * Arnold (surname), a German and English surname Places Australia * Arnold, Victoria, a small town in the Australian state of Victoria Canada * Arnold, Nova Scotia U ...
, p. 16.


References


Bibliography

* * * {{featured article Animated characters introduced in 1990 Villains in animated television series Fictional murderers Fictional assassins Fictional attempted suicides Fictional businesspeople Fictional clowns Fictional mayors Fictional stalkers Fictional Republicans (United States) Fictional television personalities Fictional Yale University people Male characters in animated series Male villains The Simpsons characters Television characters introduced in 1990 Television sidekicks