The Simpsons/Sideshow Bob Terwilliger

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Sideshow Bob Terwilliger
The Simpsons
Actor Kelsey Grammer
First Appearance The Telltale Head (cameo)
Series Billing Series: Guest Star
Episode Count 10 as of season 19
Notable Episodes Krusty Gets Busted, Black Widower, Cape Feare, Sideshow Bob Roberts, Sideshow Bob's Last Gleaming, Brother From Another Series, The Great Louse Detective, The Italian Bob, Funeral for a Fiend


Role in The Simpsons

Bob began his career as Krusty the Clown's non-speaking sidekick. He had only won the job because he proved to be a better comic foil than his younger brother Cecil Terwilliger, who had actually auditioned for the part. As the years went on, the Yale-educated Bob became increasingly angry at being overshadowed by Krusty's "dilapidated vaudeville antics" and continual abuse.

Finally, Bob snapped and framed Krusty for armed robbery at the Kwik-E-Mart. He took over Krusty's television show, introducing elements of higher culture and reading Man in the Iron Mask. Although the program was critically acclaimed, Bob's reign was short-lived, as Bart Simpson exposed his plan and landed him in jail.

Once his true character was revealed, Bob assumed the role of evil genius in The Simpsons. Episodes centered on Sideshow Bob typically involve Bob being released from prison and acting out a cunning revenge plan, which is foiled by Bart and Lisa. Frequently such plans involve attempting to kill someone, usually Bart or, less often, Krusty.

In Bob's first appearance after his failed framing of Krusty, he married Bart's aunt Selma Bouvier as part of a scheme to gain access to her stock shares, and then tried to blow her up on their honeymoon. Once again, Bart foiled Bob's plan, and Sideshow Bob returned to prison. After his second release he targeted Bart, threatening him repeatedly and forcing the Simpsons to move to Terror Lake as part of the Witness Relocation Program. Bob followed them to their new home on a houseboat and, after subduing the rest of the family, attempted to kill Bart. He allowed Bart a final request, and Bart asked him to sing the entire score of H.M.S. Pinafore. The delaying tactic leads to Bob's arrest. In another episode, Bob rigged the Springfield mayoral election, and after another escape planned to blow Springfield up with a nuclear bomb unless the city stopped broadcasting television. After this escapade, Bob was genuinely redeemed, and instead his brother Cecil attempted to commit a crime. Cecil harbored resentment because his brother had become Krusty's sidekick instead of him, and tried to frame Bob for embezzlement by sabotaging the Springfield Dam. Bob and Bart together foiled Cecil's plan and saved the town, but both brothers ended up in prison due to Chief Wiggum's stupidity.

Once again, Bob was released from prison, and developed a plot to kill Krusty using Bart as a suicide bomber but he was again foiled. Later, someone tries to murder Homer, so Bob is released from prison so he can help Homer find the culprit. After the mystery was solved, he returns to murder Bart, but finds he can not do it. Bob later moved to Italy, looking for a fresh start. There, he was elected mayor of a village in Tuscany and married a local woman named Francesca, with whom he had a son named Gino, who resembles him. The Simpsons visited and Bob welcomed them with hospitality, on the condition that they not reveal his felonious past; however a drunken Lisa did just that, alienating Bob from his citizens. His wife and son did not abandon him though, and the three swore a vendetta on the Simpsons. The entire Terwilliger family returns in a later episode, when Bob fakes his own death and attempts to burn Bart alive at his funeral. Instead, Bob and his entire family were foiled and thrown in prison, where Bob goes completely insane.

A running joke throughout his appearances after his arrest is that, when he first appears, Bart and Lisa scream "AAAHHH, SIDESHOW BOB!"

Other appearances

Alongside his appearances in the series, Sideshow Bob has made several appearances in other The Simpsons media. Kelsey Grammer recorded lines for Bob for The Simpsons Movie, but the scene in which he was to appear was cut. In The Simpsons Game, released in November 2007, Bob has a speaking cameo appearance at the end of the "Invasion of the Yokel-Snatchers" chapter. Bob was also included as a level boss in the 1991 video game "Bart vs. the Space Mutants".

Sideshow Bob plays a large 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 Bart and the other Simpsons.



Sideshow Bob first appeared in the background of a scene in the season one episode "The Telltale Head". In that appearance, his design was more simple and his hair was round in shape. His first major appearance was in season one's penultimate episode "Krusty Gets Busted". Bob's design was updated for "Krusty Gets Busted", and the animators tried to redo his scenes in "The Telltale Head" with the re-design, but did not have enough time. The script for "Krusty Gets Busted" called for James Earl Jones to voice Bob, but the producers instead went with Kelsey Grammer, then a cast member on Cheers. Bob did not say anything during the first half of "Krusty Gets Busted" because the character always spoke with a slide whistle and when he finally did speak, it would be a shock to hear Grammer's voice. Grammer used his impression of Ellis Rabb, a man for whom Grammer had once worked, for Bob's voice. For season three's "Black Widower", the writers decided to have Bob return to get revenge on Bart for foiling his plan in "Krusty Gets Busted". They took the idea of the Coyote chasing the Road Runner, and had Bob always inserting himself into Bart's life. However, he did not appear in every season because the writers were not always able to think of reasons to bring Bob back.

Brad Bird first designed Bob for "Krusty Gets Busted". As the episode's animation progressed he made Bob sleeker, more urbane and refined, and worked with Grammer's voice. For "Black Widower", David Silverman updated the model to reflect the animation of Bird. Despite common fan belief that Bob was named after Terwilliger Boulevard in Portland, Oregon, Dan Castallaneta says Matt Groeining named him after the character Dr. Terwilliker from the film The 5,000 Fingers of Dr. T.


Kelsey Grammer initially thought that Bob would be a one-time character, and calls him "the most popular character I've ever played." The writers believe that Grammer has a great voice and try to create something for him to sing each time he appears. Grammer usually comes in for table readings, although when he cannot, Greg Berger stands in for him. Former Executive producer David Mirkin found Grammer a joy to direct as he was very funny, but noted that he hates doing the evil Sideshow Bob laughs. A rule for the early episodes that featured Bob was that there had to be a recap of his evil deeds in case the viewers did not remember them. The concept was dropped in later episodes.

Sideshow Bob's theme, which is used whenever Bob gets out of prison, was first used in the season five episode "Cape Feare", Bob's third episode. It is based on the score of the movie Cape Fear, which was composed by Bernard Herrmann. The musical score for "Cape Feare" earned composer Alf Clausen an Emmy Award nomination for "Outstanding Dramatic Underscore - Series" in 1994. Bob's prisoner number is often 24601, which is Jean Valjean's prisoner number in Les Miserables. Another trademark for Bob is to step on rakes, a joke that first appeared in "Cape Feare". In that episode, Bob stepped on nine consecutive rakes, which the writers added to fill up time. The sequence has become known as the "rake joke" and has been referred to as being "genius in its repetitive stupidity".

Bob's brother Cecil made his first appearance in the eighth season episode "Brother From Another Series". He is voiced by David Hyde Pierce, who played Frasier Crane's brother Niles in Frasier, and Bob and Cecil's interactions were based on Niles' and Frasier's. Cecil returned in "Funeral for a Fiend" in season 19, along with their previously unseen father, Dr. Robert Terwilliger, who was played by John Mahoney. Mahoney played the father of Grammer and Pierce's characters in the series. Bob also has a wife named Francesca (voiced by Maria Grazia Cucinotta) and a son named Gino, both of whom were introduced in the season 17 episode "The Italian Bob", and both of whom returned for "Funeral for a Fiend".