Sideshow Bob
Robert Underdunk Terwilliger Jr., PhD,[a] better known as Sideshow Bob, is a recurring character in the animated television series The Simpsons. He is voiced by Kelsey Grammer and first appeared in the episode "The Telltale Head". Bob is a self-proclaimed genius who is a graduate of Yale University and a champion of high culture, including the adoption of a transatlantic accent, similar to that of Grammer's portrayal of Dr. Frasier Crane from the sitcoms Cheers and Frasier. He began his career as a sidekick on Krusty the Clown's television show, but after enduring constant abuse, Bob framed his employer for armed robbery in "Krusty Gets Busted", only to be foiled by Bart Simpson, and sent to prison. Bob started seeking revenge against Bart while in prison, and the two became feuding arch-enemies.
Sideshow Bob
"The Telltale Head" (1990)
Matt Groening
Robert Underdunk Terwilliger Jr.[a]
Male
Television personality
Former Mayor of Springfield
Former Mayor of Salsiccia
Scientist
Professor
Actor
Criminal
Dr. Robert Terwilliger Sr. (father)
Dame Judith Onderdonk (mother)
Cecil Terwilliger (brother)
Selma Bouvier (ex-wife)
Francesca (wife)
Gino (son)
Patty Bouvier (ex-sister-in-law)
Marge Simpson (ex-sister-in-law)
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. 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. In season 27, however, during the first segment of "Treehouse of Horror XXVI", 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.[4][5][6]
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".[7] 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 and John Mahoney, respectively, echoing the roles they played in Frasier. Grammer, who based Bob's voice on that of actor Ellis Rabb, 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 season 35, Sideshow Bob has appeared in more than 40 episodes, had speaking appearances in 24 of these, and been featured as the main character in 14. The most recent of the latter, "Bobby, It's Cold Outside", aired during the 31st season, and his most recent speaking appearance was in "Treehouse of Horror XXXIV" in the 35th season.[8] 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, and stars as the main antagonist in The Simpsons Ride at Universal Studios' theme parks. A lover of Gilbert and Sullivan operettas, Sideshow Bob is also known for his singing voice; several of Grammer's performances have been included in The Simpsons musical compilations.
Appearances[edit]
On The Simpsons[edit]
The character of Sideshow Bob began his career as the non-speaking sidekick who would only use a
whistle
on Krusty the Clown's television show.[9] Bob first appears in "The Telltale Head" (season 1, 1990). In the episode, he and Krusty plan a big event for whoever knows information of who captured the head of Jebediah Springfield's statue, and joins in on the town mob when it is discovered that Bart Simpson took it. However, after repeated instances of abuse, including being shot from a cannon and hit constantly with pies, the Yale-educated Bob became angry at Krusty and resentful of the clown's success. In "Krusty Gets Busted" (season 1, 1990), Bob disguised himself as Krusty and framed him for armed robbery of the Kwik-E-Mart. After Krusty is arrested, Bob takes control of the show, introducing children to elements of high culture. However, Bob's reign is short-lived; Bart exposes him as the robber, Krusty is released, and Bob is fired and sent to jail.[10]
In "Black Widower" (season 3, 1992), Bob's first major appearance after framing Krusty, he is released from prison and marries Bart's aunt Selma Bouvier as part of a scheme to inherit money she has invested in the stock market. Bob attempts to blow Selma up during their honeymoon, but Bart again foils the plan and Sideshow Bob returns to prison.[11]
After being paroled from prison in "Cape Feare" (season 5, 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 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. 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.[12]
Bob is released from prison once again in "Sideshow Bob Roberts" (season 6, 1994), and runs for Mayor of Springfield as the Republican Party candidate. He defeats Democratic Party incumbent Joe Quimby in a landslide, but Bart and Lisa discover from Waylon Smithers 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.[13]
Sideshow Bob escapes from prison for the first time in "Sideshow Bob's Last Gleaming" (season 7, 1995), and threatens to blow up Springfield with a nuclear 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). This too is thwarted, and Bob returns to prison.[14]
In the following season, Bob takes advantage of the prison's work release program, and appears to be genuinely redeemed. "Brother from Another Series" (season 8, 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.[15] Reverend Lovejoy declares him a changed man and recommends him for a 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 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.[15]
Bob returned in "Day of the Jackanapes" (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 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 and reconciles with Krusty, although he is returned to prison for it.[16]
Bob's aid is sought by Springfield police in "The Great Louse Detective" (season 14, 2002). After an attempt is made on Homer Simpson'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 [Bart's] face" and cannot do it.[17]
In "The Italian Bob" (season 17, 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 and marries a local woman named Francesca, with whom he has a son named Gino. The Simpson family, in Italy to retrieve a car for Mr. Burns, 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 with him on all the Simpsons.[18]
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 Onderdonk, 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, which he attempts to cremate at the otherwise empty funeral home as all the Terwilligers laugh maniacally. They are foiled by Lisa and the rest of the Simpson family and sent to prison.[19]
In "Sex, Pies and Idiot Scrapes" (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 (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.[20]
In "O Brother, Where Bart Thou?" (season 21, 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" (season 21, 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.[21]
Bob appears in "At Long Last Leave" (season 23, 2012), the 500th episode of The Simpsons. He attends a town meeting to decide if the Simpson family should be banished from Springfield, and is one of many who express their desire for it to happen.[22] He makes a silent appearance in "Moonshine River" (season 24, 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, 2014), he was revealed to be a Chief Scientist for a genetic engineering 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, but Bob reveals that he has also genetically modified himself to give himself various superhuman abilities, intending to acquire DNA from the relics of various historical figures stored in the Springfield Museum to make himself a superhuman dictator. 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 gills he gave himself allow him to live.
Bob also appears in "Clown in the Dumps" (season 26, 2014). Having returned to prison, he offered his condolences to Krusty after the death of his father, Rabbi Krustofsky. Several episodes later, Bob returned in "Blazed and Confused" (season 26, 2014), where he meets Mr. Lassen, Bart's former teacher, who was now reduced to working in prison as a guard 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" (season 27, 2015), in the first segment called "Wanted: Dead, then Alive", Bob uses Milhouse'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" (season 27, 2016), grunting in annoyance as he wipes off Bart's graffiti from Hettie Mae Boggs' promo poster on the wall along with Snake Jailbird and other inmates.
Bob returns in "Treehouse of Horror XXVII" (season 28, 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, except Grimes's ghost. In the ending sequence, Bob is one of the characters featured in the "600" song played by Judith Owen. In "Havana Wild Weekend" (season 28, 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" (season 28, 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, 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, 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" (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" (season 33, 2022), where he is seen signing the chests of citizens like Milhouse's father Kirk Van Houten at the celebration of Krusty Burger's 50th anniversary, a callback to the "Die Bart, Die" scene from "Cape Feare".
In the "Treehouse of Horror XXXIV" segment "Ei8ht" (season 35, 2023), in an alternative ending to "Cape Feare", Bob realizes that Bart is stalling his death by making him sing Pinafore, and as a result, kills him, traumatizing Lisa. 30 years later, the Springfield Police asks Professor Lisa Simpson to look into a series of murders committed by an unknown serial killer. Perplexed, Lisa seeks Bob's help, but Bob just mocks Lisa. Later, Lisa realizes she herself has done all the murders. Bob is transferred to another prison cell to find Lisa waiting for her, revealing that a split personality emerged after the death of Bart and that she had committed all those murders in hopes of going to prison with Bob. To the music of H.M.S. Pinafore, Lisa gleefully slashes Bob to death.
Other media[edit]
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, but the scene was cut; the deleted scene shows him amongst the angry mob, intent on killing Bart until he learns that the mob is apparently after Homer only, prompting him to leave in disappointment.[23] Sideshow Bob has made regular appearances in the monthly Simpsons Comics,[24] and several of Kelsey Grammer's singing performances have been included in The Simpsons CD compilations. His performance of the H.M.S. Pinafore in "Cape Feare" was later included on the album Go Simpsonic with The Simpsons,[25] and the song "The Very Reason That I Live" from "The Great Louse Detective" was included on The Simpsons: Testify.[26] A previously unaired song, "Hullaba Lula", originally written for "Day of the Jackanapes", was also included on that compilation.[26] The producers modeled the song after "Zip-a-Dee-Doo-Dah", but were forced to remove the song from the episode when they were unable to obtain the rights to it.[27]
In The Simpsons Game, released in November 2007, Bob has a speaking cameo appearance at the end of the chapter titled "Invasion of the Yokel-Snatchers" in which he was working with Kang and Kodos.[28] Sideshow Bob appears in the 1991 The Simpsons Arcade Game, 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.[29] Sideshow Bob plays a lead role in The Simpsons Ride, which opened at Universal Studios Florida and Universal Studios Hollywood 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.[30][31]
In The Simpsons: Tapped Out, a city-building game 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. 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 Onderdonk, Captain Bob, and Opera Krusty. Most of the event action takes place at Monsarno Research and Opera House.