Sideshow Bob

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The Simpsons character

Robert Underdunk "Sideshow Bob" Terwilliger
Age	Appears to be in his Late 30s to mid-40s
Gender	Male
Hair color	Red and wild
Job	Unknown
Relatives	Brother: Cecil Wife: Francesca Son: Gino Ex-wife: Selma Bouvier
First appearance	The Telltale Head (cameo) Krusty Gets Busted
Voice actor	Kelsey Grammer

Robert Underdunk Terwilliger, better known by his stage name Sideshow Bob, is a fictional character on The Simpsons. He is voiced by Kelsey Grammer, who won an Emmy for the role in 2006.

He was originally Krusty the Klown's TV sidekick, and was often fired out of a cannon. (He also communicated solely with a slide-whistle, despite being well-spoken).

He has since become a villainous homicidal maniac. He is known for his abnormally large feet and hair, which give him the appearance of a palm tree, as well as his grandiloquence and inability to actually kill anyone, especially his archenemy Bart Simpson. It should also be noted that he has a tendency to walk onto the bottom of rakes, causing them to spring up and hit him in the head.

Matt Groening has stated that the character was named after SW Terwilliger Boulevard in Portland, Oregon.^{[citation needed]}

Spoiler warning: Plot and/or ending details follow.

1 Biography
2 Trivia
3 "The Sideshow Bob Episodes"
4 Minor appearances
5 Notable comic book appearances
6 References

[edit] Biography

Bob never anticipated a career in show business. His younger brother Cecil (voiced by Grammer's Frasier co-star David Hyde Pierce) auditioned for the role of Krusty's sidekick, having wanted to act in that capacity since the age of five. However, Krusty thought Bob's upright demeanour would make him a better comic foil, and gave him the job instead. It should be noted that Bob was only there to give Cecil moral support.

As the years went on, the highly-educated Bob became increasingly angered at being overshadowed by Krusty's 'dilapidated vaudeville antics', not to mention Krusty's continual abuse. Finally, he snapped and framed Krusty for armed robbery. He took over the show, making it more upmarket (for example, Krusty's catchphrase 'Children, who do you love?' was replaced by the grammatically correct 'Whom do you love?') introducing culture, singing Cole Porter, and reading the classics ('Man in the Iron Mask', etc.) to his rapt young audience. Although the show earned critical raves -- and boffo ratings -- his reign was shortlived, as Bart exposed his plan and landed him in jail.

Since then, he has taken the position of Evil Genius in the series -- a typical Sideshow Bob episode involves his being released from incarceration and acting out some cunning plan, which is foiled by Bart, and (usually) his sister Lisa. Frequently this plan involves killing someone: Krusty, Bart or everyone in Springfield. Bob has been eager to get revenge on Bart for foiling his schemes, but in The Great Louse Detective, when he had the opportunity to kill Bart, he found himself unable to, as he had 'grown accustomed to Bart's face' (an homage to My Fair Lady). Bob seemingly has become used to the urge to kill Bart, and having his schemes foiled by him, and apparently can't bring himself to end their rivalry.

Bob was briefly married to Selma (whom he also tried to kill). He is a staunch Republican, and was briefly mayor of Springfield, as well as briefly the mayor of a village in Tuscany, Italy. He can sing entire Gilbert and Sullivan operettas off the cuff, and in The Italian Bob sang the climax of Vesti la Giubba after having Krusty fall through a trapdoor during his performance of the title role of Pagliacci. He also has a tendency to step on rakes, as evidenced in both Cape Feare and Day of the Jackanapes. Bob was also married to an Italian woman at some point prior to 2005, with whom he has his son Gino.

Bob is surprisingly multitalented, able to speak Sanskrit, French, German, Spanish and Italian, sing surprisingly well (leading a prison production of Evita and giving an off-the-cuff rendition of H.M.S. Pinafore), perform skilful acrobatics and pantomime (as shown on the campaign trail when running for mayor), read Alexandre Dumas, père, cite Buddhist philosophy, and generally be highly educated and intellectual. Bob had accepted Krusty's job offer with the hopes of creating high-quality children's programming that would enlighten and nurture young minds, but became bitter and disillusioned after years of Krusty's abuse and lowbrow shenanigans. As Bob himself put it, "my foolish capering destroyed more young minds than syphilis and pinball combined!" He seems very disgusted with the state of American culture, for example remarking on how far aviation has fallen from "the days when it was a gentleman's pursuit... back before every Joe Sweatsock could wedge himself behind a lunch tray and jet off to Raleigh-Durham."

Bob also has several tattoos, such as 'Die Bart Die'. He claims this is German for 'The Bart, The', which led to his being granted parole on the grounds that "no one who speaks German could be an evil man". However, even on the highly unlikely chance that this is actually true, Sideshow Bob uses the wrong word for "the"; "Die Bart, Die" is inaccurate. In German it would be "Der Bart, Der", ("Bart" also happens to be the German word for beard). On his chest is another tattoo showing Bart's decapitated head on a skateboard, and on his back is a tattoo with a word bubble saying 'Ouch, Man'. The tattoos on Bob's fingers parody those of Robert Mitchum's character in The Night of the Hunter (whose fingers are tattooed L-O-V-E and H-A-T-E), but, as Simpsons characters have only three fingers (besides the thumb), Bob's finger tattoos spell 'L-U-V' and 'H-Ā-T'.

Bob's brother Cecil has harbored resentment for winning the role of Krusty's sidekick for many years, and during one of Bob's releases from prison, tried to frame him for embezzlement and sabotaging the Springfield Dam. Cecil's plan ended with mixed results: the sabotage did not destroy Springfield as expected, and both brothers took the blame for it. During the same episode it was revealed that Cecil attended Princeton University for four years (derided as 'Clown College' by Bob), whereas Bob had already been established as a proud graduate of Yale (like Mr. Burns). Like the two brothers, these Ivy League schools have a long-standing rivalry. The character of Bob is much like Grammer's alter-ego Frasier Crane as they both enjoy the arts, attended Ivy League schools and speak with immaculate grammar and pronunciation. Their only differences are in politics as Bob is a staunch Republican whereas Frasier is a liberal.

Unlike his brother, he won political office. Following a successful campaign by Rush Limbaugh-clone Birch Barlow to secure his release as a "persecuted conservative," he ran against Mayor Quimby, defeating him thanks to his skills in electoral fraud. He quickly used his new office to divert the newly-planned Matlock Expressway to force the razing of the Simpson home. His scheme was thwarted when his usual adversaries tricked him into revealing the multi-volume 'Bob's Fraud Log' to a judge. When the judge asked him why, he told him that it was to save the people from themselves, in a speech parodying Jack Nicholson's iconic "You can't handle the truth" monologue from A Few Good Men. This did not save him as he returned to prison, albeit a minimum security facility where he got the opportunity to compete in rowing competitions against the alumni of Ivy League universities.

Later on in the series, Bob decides to give himself a fresh start, so he becomes mayor of a village in Tuscany. He marries an Italian woman and also has a child who is just as evil as he is. When the Simpson family comes to visit Italy, Bob welcomes them with hospitality on the condition that they not reveal his felonious past. However Lisa, while drunk, reveals Bob's past in America, alienating him from his citizens and prompting him to swear a vendetta on the Simpsons. He and his family pursue the Simpsons, but the Simpsons eventually escape to America with help from Krusty the Klown. He and his family merely walk away, but it is likely that they still want to get rid of the Simpsons.

Kelsey Grammer has revealed that Sideshow Bob will make an appearance in the upcoming Simpsons movie.^[1]

In "Black Widower" Bob received an Emmy award for his work on the Krusty the Clown Show for Best TV Clown Sidekick. Because he got it while in prison it was taken away from him. Kelsey Grammar also received a 2006 Emmy award for Best Voice Over for playing Bob.

[edit] Trivia

Bob is one of the few Simpsons characters who has no "standard" outfit. In most episode he wears different colors and styles of clothing depending on the circumstances.
In Krusty Gets Busted, Bob is on the show "Choices", which resembles the sitcom Cheers on which Kelsey Grammer appeared for many years.
Whenever Bob is revealed to the audience, the same musical cue is played. This is known as a leitmotif, and Bob's is one of the only uses of this musical style in the series.
In most of Bob's devious plans, along with Bart, Lisa is also responsible for his convictions, such as in the episode The Italian Bob. However, Sideshow Bob only seeks revenge on Bart Simpson rather than Lisa and even states that he feels "fairly indifferent" towards her (Sideshow Bob's Last Gleaming).
Bob's criminal number is 24601, the number given by Victor Hugo to the principal character Jean Valjean in Les Miserables.
Bob reads Prison Bride Magazine in his cell that he shares with Snake in some episodes, although his cellmates seem to vary.
In German-dubbed episodes of the show, Sideshow Bob is called Tingeltangel Bob ("honky-tonk Bob").
In season 1 all episodes before Krusty Gets Busted Bob was seen with an afro, but the creators changed it because they felt a 'Banana Tree' hairstyle was more diabolical.

[edit] "The Sideshow Bob Episodes"

Sideshow Bob is a unique character in The Simpsons as he only appears in occasional episodes where he is clearly the star. Unlike most other characters, he rarely appears as a "background" character, and almost never has a "minor role" in any episode's plot. This can be explained by the fact that Bob is in prison most of the time.

Episodes where Bob appears in a main role are thus known by fans as Sideshow Bob Episodes because of their unique status.

Krusty Gets Busted: Sideshow Bob's villainous debut. His hair has changed from an afro to a palm tree fronds hairdo. Krusty the Clown is framed for robbing the Kwik-E-Mart, and the entire town abandons him and embraces his replacement, the suave, sophisticated Sideshow Bob. However, Bart never loses hope in Krusty and is eventually able to unmask the identity of the real culprit ... Sideshow Bob.
Black Widower: Selma begins dating her prison pen pal, who the Simpsons discover is none other than Sideshow Bob. Sideshow Bob declares that he has been reformed by Selma's love, and eventually proposes to and marries her (all to the objection of Bart, who still believes Sideshow Bob is pure evil). On their honeymoon, it is revealed that Sideshow Bob only wants to kill Selma for her insurance money, but Bart manages to unravel his scheme and stop it at the last second, sending Sideshow Bob back to prison.
Cape Feare: Bart receives a series of threatening letters written in blood, and soon afterwards Sideshow Bob is released from prison on parole. Discovering that he is responsible for the threats and is planning to kill Bart, the Simpsons go into the witness protection program and move to Terror Lake, but Sideshow Bob follows them. After a few days of stalking, Sideshow Bob finally sneaks into the Simpson's new home to kill Bart. The two end up confronting each other on the deck of their small houseboat, but Bart manages to outwit Sideshow Bob by asking him to sing the entire score to the H.M.S. Pinafore as a last request. This delays Bob long enough for the boat to crash, where a waiting Chief Wiggum arrests him (telling Bob "It's a good thing you drifted by this brothel"). This episode also features the first scene with Bob's slapstick act of accidentally stepping on numerous rakes, which hit him in the face. This episode is largely a spoof of the 1991 remake of the 1962 thriller Cape Fear.
Sideshow Bob Roberts: Sideshow Bob's outspoken and eloquent conservative viewpoints cause the town Republicans to parole him and get him to run for Mayor against Quimby, where he wins in a landslide (one of the arguments against Quimby being that he agreed to parole known criminal Sideshow Bob). Sideshow Bob uses his new power to make the Simpson family suffer, scheduling their home for demolition and putting Bart in Kindergarten (though this actually makes Bart happier). Lisa discovers that Sideshow Bob won the election by registering dead people to vote for him. Lisa and Bart confront Sideshow Bob with the truth, and Sideshow Bob is arrested and sent back to jail.
Sideshow Bob's Last Gleaming: Sideshow Bob's hatred of television prompts him to steal an atomic bomb from the Springfield Air Base, and he threatens to destroy all life in Springfield unless television is permanently cancelled. Krusty violates the cancellation, so Sideshow Bob attempts to detonate the bomb, but it turns out to be a dud ("best before November 1959"). Sideshow Bob then takes Bart as a hostage and goes off on a kamikaze mission aboard the Wright Brothers' plane to kill Krusty, but is foiled by the frailty of the Wright flyer.
Brother from Another Series: Sideshow Bob is released from prison and enters into a work-release program headed by his brother Cecil played by David Hyde Pierce Grammer's co-star and fictional brother from the television series Frasier. The program is a construction project working on the new Springfield Dam. Bart and Lisa believe Sideshow Bob is planning something terrible, and spy on his every move. The two run across evidence that suggests Sideshow Bob is planning to wipe out Springfield by sabotaging the dam. Eventually, it is revealed that Sideshow Bob really has reformed, and that it is his brother Cecil that is planning on destroying Springfield to frame Bob as revenge for 'stealing' the position of Krusty's sidekick from him (but mostly for the money he made from using cheap materials for the dam). Bart, Lisa, and Sideshow Bob team up to stop Cecil's plan, and Bart even saves Sideshow Bob's life when the dam begins to collapse. Moved, Sideshow Bob promises to stop trying to kill him. However, Sideshow Bob ends up taking an equal share of the blame for Cecil's scheme, and both of them are hauled off to jail by Wiggum.
Day of the Jackanapes: Krusty the Clown becomes sick of annoying network executives, prompting him to arrange for a final episode. Meanwhile, Sideshow Bob is enraged when he learns that Krusty has destroyed all evidence of his existence by taping over his old episodes (since Krusty had a love for Judge Judy and didn't want to buy blank tapes), prompting him to enact yet another "kill Krusty" scheme, this time by hypnotizing Bart into becoming a suicide bomber and killing Krusty on the show. During the initial hypnosis, he continues with his 'Walk into a rake and shudder' act, proclaiming the rake to be his greatest arch-enemy in his life beyond Bart. However, at the last minute, Krusty makes an on-air apology to Sideshow Bob for all the pain he's caused him, causing Sideshow Bob to have a change of heart. Sideshow Bob warns everybody that Bart has a bomb, prompting Krusty's pet monkey, Mr. Teeny, to swoop in and throw the bomb away (the only people hurt are the network executives, whose body parts merge into a T-1000-like monster). Sideshow Bob and Krusty finally resolve their differences, but Sideshow Bob is still scheduled to be decapitated for his crimes by Chief Wiggum (although the show cuts to the credits before we see the impact). He must have survived somehow, though, because he next appears in:
The Great Louse Detective: A series of attempts on Homer's life prompts Chief Wiggum to consult Sideshow Bob as a Hannibal Lecter-style expert on the criminal mind. Sideshow Bob is eventually sent to live with the Simpsons to help reveal the killer's identity, with an electric shock device strapped to him to prevent him from causing trouble. In a final confrontation at Mardi Gras, Sideshow Bob saves Homer's life and the two confront the real killer: Frank Grimes Jr. In the end, Sideshow Bob sneaks into Bart's room and is about to kill him, but finds that he can't do it because he's "grown accustomed to Bart's face" a la My Fair Lady. He later escapes, but not before receiving a number of electric shocks from the misplaced controller of his electronic bracelet.
The Italian Bob: When the Simpsons visit a small Italian village, they find that Sideshow Bob is the mayor. His new wife and son - Francesca and Gino - know nothing about his murderous life in America, although Gino says "Die, Bart!" several times (apparently Bob is known to yell it in his sleep). Bob begs the Simpsons not to tell anyone. They trust that he has changed, and they agree. However, when Lisa gets drunk at a party, she reveals everything. All three Terwilligers end up vowing revenge (or "vendetta") on the Simpsons, apparently renewing Bob's murderous wishes. The Simpsons are nearly killed in the Colosseum, but Krusty saves them at the last minute. In this episode, it was implied that Bob experimented with homosexuality while in college. This episode may or may not draw inspiration from The Mayor of Casterbridge, in which a Mayor has similar familial secrets.

[edit] Minor appearances

The Telltale Head: First appearance of Sideshow Bob as Krusty the Klown's much-abused sidekick. Bob only appears briefly on Bart's television and has no speaking lines. His hair is an afro. He is also among the people gazing up at the statue of Jebediah Springfield, where his hair has become a palm tree head.
Bart Gets an F: Sideshow Bob is among the crowd of people joining hands and caroling (ignoring the fact that he's in jail).
Bart the Murderer: When Bart is thrown in jail, Sideshow Bob is shown as his buffed-up cellmate. However, Bob has no lines and does not do anything to Bart in this cameo, other than shoot him a dirty scowl.
Lisa's First Word: In a flashback to 1984, Bob is seen briefly on Krusty's show. His hair is rendered the same shade of teal as Sideshow Mel's. He does not have any lines.
Another Simpsons Clip Show: One of the clips shown is Sideshow Bob and Selma on their honeymoon in the episode "Black Widower".
Pokey Mom: While in a prison infirmary Bob is seen wearing a full headcast. Later Marge tells Bart that Sideshow Bob would be seeing him real soon. Bart just laughs this off. ("Oh, that Bob"). Bob would indeed encounter Bart again a month later in Day of the Jackanapes.
In This Little Wiggy, when Bart and Ralph are looking through Chief Wiggum's prison files, one of the manila folders is labelled "Terwilliger, R." with the R standing for Robert, thus referring to Sideshow Bob.
Sideshow Bob appears on the promo card for Large Marge, but does not appear in the episode.
A couch gag in Mobile Homer featured Bob seated on the couch with the family, disguised as Homer, and then revealing himself by whipping off a rubber mask and chasing Bart with a knife.
Bob, in prison, makes a brief appearance in the Do the Bartman music video.
Bob appeared in a TV Guide promotional image for The Mook, the Chef, the Wife and Her Homer. He was shown glaring at a terrified Bart. However, he did not appear in the episode.
Bob makes a brief cameo in the Springfield Gorge level of the Simpsons arcade game. Surprisingly, he provides a health-restoring turkey to the players rather than trying to kill them. In other Simpsons video games where he appears, he is usually a level boss.
Sideshow Bob's face is shown among the photos of those banned from the comic book shop, including Bart and Milhouse, forever by the Comic Book Guy in Worst Episode Ever.

[edit] Notable comic book appearances

"Simpsons Comics" #2: When Bart and Milhouse are sent to jail as part of the school program, they end up in the same cell as Sideshow Bob is in. Bart slips out only to end up on a chain gang, where he is cuffed to Bob. He attempts to murder him but gets foiled.
"Simpsons Comics" #26: Bob attempts to prove to Springfield the dangers of school buses by installing a spring-loaded seat on Otto's bus, specifically Bart's seat.
"Simpsons Comics" #41: From within his prison cell, Bob attempts to ruin Krusty by using a computer to hack into the operation of Krusty's newly-opened "Krusty Brand Fun Factory". Bob's brother Cecil also appears as his cellmate.
"Simpsons Comics" #46: Bob is released from jail for good behavior. He opens his own crime school with Nelson, Dolph, Kearny, Jimbo and Bart as his students, but he gets overconfident and tossed back in jail.
"Simpsons Comics" #57: Seen in talk show about criminals hosted by Kent Brockman.
"Simpsons Comics" #77: Released from jail and attempts to murder Bart, but plan foiled by Sideshow Mel.
"Simpsons Comics" #114: Seen in prison and briefly escapes on the final page of the issue, hiding in the sewers.
"Simpsons Comics" #123: Once more tries to kill Bart.
"Bart Simpson's Treehouse of Horror" #2: Given a shot by Dr. Nick to supposedly cure his cold, but winds up transforming into a giant blob monster. Bob consumes Springfield, but is foiled when his weakness for classical music distracts him long enough for Bart to flush him down the sewers