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Villain Overview

Hello, Bart.
~ Sideshow Bob's catchphrase.

Robert Underdunk Terwilliger Jr., better known as Sideshow Bob, is the secondary antagonist of The Simpsons franchise, appearing as the secondary antagonist of the animated sitcom series The Simpsons and the main antagonist of The Simpsons Ride.

He is a former television personality on The Krusty the Clown Show turned criminal mastermind. He is the archenemy of Bart Simpson and Krusty the Clown as he desires to kill them both, the former for foiling his schemes and the latter for constantly abusing him in the show. Although he doesn't want to just go after Bart, he wants to go after the rest of the Simpson family and kill them.

He has constantly come up with multiple evil plans, such as framing Krusty for robbery, hunting down Bart and attempting to become mayor and continues to serve as an attempted murderer and a criminal.

He is voiced by Kelsey Grammer, who later played Stinky Pete in Toy Story 2, Rothbart in Barbie of Swan Lake, Harold Attinger in Transformers: Age of Extinction and Hunter in Storks.


Sideshow Bob started out as the mute sidekick of children's show host Krusty the Clown. Bob abusively went through an act that involved being shot out of a cannon by Krusty himself, all the while being deemed hilarious to the child audience.

Finally having enough, Sideshow Bob disguised himself as Krusty and robbed the Kwik-E-Mart and framed him, resultng in the clown being arrested and Bob being made the new host of his show. The only main character who witnesses the act in the Kwik-E-Mart was Homer Simpson.

However, Bob's victory was to be short lived. Not long after the robbery, Bob began shooting an interview on Krusty's condition with Bart Simpson, Homer's son. As Bob began a speech on Krusty's 'behalf', it was then that the pieces of the puzzle finally connected in Bart's brain, slowly figuring out that Sideshow Bob was behind the robbery all the time and that he framed Krusty for it. The young Simpson then exposed Bob to the authorities and had him arrested.

This was not the end, however, as Sideshow Bob swore revenge on Bart as he was taken away, becoming the boy's nemesis.

Rivalry with Bart

See Sideshow Bob/Synopsis


Sideshow Bob is a complex character in the series. He is a sadistically obsessed psychopath by trying to kill Bart Simpson, yet he is often very smart and sophisticated in talk, and has shown redeeming features in the past such as deciding against killing Krusty when he realized that he regretted mistreating him (which led to his start to villainy). He also doesn't want to kill only Bart, he wants to kill the Simpson family. His main target besides Bart, is the Simpson family.

Sideshow Bob enjoys the finer things in life, including reading classical literature and possesses massive intellect. Likely due to his upbringing, he has a passion for theater, knowing Gilbert and Sullivan's H.M.S. Pinafore by heart as well as Shakespeare's works. In contrast to his love of the "higher pleasures", he despises television and other "low class" things, which gives him a rather snobbish attitude. Ironically, in the time when he was a master criminal, he studied the uses of dynamite, which would theoretically be considered low class. At times, he also seems to possess genuine desires to help humanity, as he explains that his motivation for tricking the Springfield citizens into electing him was to "save them from themselves".

In addition, when he briefly took over Krusty's show after framing Krusty for armed robbery, he attempted to insert more high culture into the show (i.e. reading to the child viewers from the classic novel The Man in the Iron Mask) in an attempt to encourage children's intellectual development, and his plot to threaten Springfield with a nuclear bomb unless they abolished television was done because he saw just what a negative, mind-numbing effect television can have on people and thus believed that forcing the people of Springfield to abolish it would be greatly beneficial to them in the long run.

Along those lines, in an interview with the "Star Wars Insider" magazine, a couple of the Simpsons producers were asked if there were any Springfield characters who disliked Star Wars. One of them initially said Sideshow Bob, but the other corrected him that Bob would very much appreciate that Star Wars contains themes on the importance of young people going out into the world and making something of themselves.

Beneath the cultured gentlemen is the heart of a cold-blooded killer; Bob is a prejudicial man who is willing to hurt others to get what he wants. Bob's primary motive seems to be revenge; his original crime (framing Krusty the Clown) was an attempt to get back at him for making a clumsy fool of Bob for years as his sidekick, and most of his other crimes have been more evil attempts at murdering Bart Simpson for foiling him. However, he has made several attempts at acquiring money and/or power not related to his vendetta against the two of them, such as when he tried to kill Selma Bouvier (though since Selma was not well-liked, this was a bit justified) or run a campaign for mayor as a Republican (if for no other reason than to make the Simpsons miserable).


Bob is a tall, slim man who is easily recognized for his pale skin, abnormally large feet and his thick, red palm-tree shaped hair that springs out of his head. When not in jail and wearing the standard orange prison jumpsuit and brown shoes of Springfield Penitentary inmates Bob usually has a rather casual but still smart sense of fashion. When he was Krusty's sideshow he was shirtless and wore a grass skirt and red clown shoes and as a mayor he wore a stone grey suit with a red tie and light blue shirt with brown shoes.

In Other Media

  • Bob also has a brief cameo appearance in the Simpsons/Family Guy crossover episode, as one of many of Bart's enemies (along with Apu) that Stewie Griffin kidnaps and tortures.
  • Sideshow Bob was the main antagonist on the ride at Universal Studios, The Simpsons Ride. While Krusty was looking for a family to choose to be the first one to try out his all new, Upsy-Downsy-Spinsaroundsy-Teenoperatied Thrill Ride, Bob steps on Homer's foot causing him to shout "D'OH!". This causes Krusty to choose the Simpson Family and also allows them to pick another group to come with them, which Bart chooses to be the audience. Sideshow Bob laughs evilly as the Simpson Family goes with Krusty as he was planning to use Krusty's new thrill ride as part of his new plan to kill the Simpsons for foiling him. Bob knocks out Krusty when the Simpsons were in the vehicle boarding station and then takes over the park and tries to kill the family (and the audience) while they crashed through different parts of Krustyland. But at the end of the ride, Sideshow Bob gets crushed by the Simpsons' couch when the family fell down the death drop. It is unknown what happened to him after that, but it is probable that he was then caught and arrested for his villainous actions and sent back to jail.
  • Bob is a supporting antagonist in The Simpsons Game, where he works for Kang and Kodos.


  • James Earl Jones was originally cast as Bob before the producers chose to have Kelsey Grammer voice the character.
  • He never made an appearance in The Simpsons Movie. However, Kelsey Grammer voiced Bob in a deleted scene that is still unreleased for unknown reasons.
  • Originally, he was set to die in Season 25 and never appear again in future episodes; but for an unknown reason, he did not die.

External Links


               The Simpsons Logo.svg Villains

Springfield Republican Party
Mr. Burns | Birch Barlow | Lindsey Naegle | Count Dracula | Blue-Haired Lawyer | Waylon Smithers

Terwilliger Family
Cecil Terwilliger | Dame Judith Underdunk | Francesca Terwilliger | Gino Terwilliger | Robert Terwilliger Jr. | Robert Terwilliger Sr.

Springfield Mafia
Fat Tony | Fit Tony | Johnny Tightlips | Legs | Louie | Don Vittorio D'Maggio | Frankie the Squealer | Johnny the Snitch | Nicky Bluepants Altosaxophony | Joey | Dante Calabresi Sr. | Dante Calabresi Jr. | Primo | Shotgun Pete

Environmental Protection Agency
Russ Cargill

Globex Corporation
Hank Scorpio | Miss Goodthighs

Recurring Characters
Agnes Skinner | Artie Ziff | Baby Gerald | Constance Harm | Dolph Starbeam | God | Hans Sprungfeld | Herman Hermann | Itchy | Jessica Lovejoy | Jimbo Jones | Kearney Zzyzwicz | Jack the Ripper | Mr. Largo | Nelson Muntz | Patty & Selma Bouvier | Senator Mendoza | Snake Jailbird | Space Mutants | Wainwright Montgomery Burns | Gina Vendetti

Treehouse of Horror
Bart (Fly) | Burnsiverse | Count Burns | Zombies | Gremlin | Groundskeeper Willie | Homer's Clones | Hugo Simpson II | Jonathan Frink Sr. | Kang and Kodos | Killer Toupée | King Snorky | Killer Krusty Doll | Lard Lad | Muttonchop Murderer | Ned Flanders | Seymour Skinner | The Blob | The Devil | Dr. Julius Hibbert | Bill the Kid | Moe-Looking Satan | The Grand Pumpkin | Witch Marge | Rachel | Maggie Simpson

Guest Star Characters
Simon Cowell | Will Wright | Bill Cipher | Variant L1130

Other Characters
Adil Hoxha | Adolf Hitler | Andy Hamilton | Baby Button Eyes | Bart Simpson's Creatures | Blue-Eyed Man | Bob Arnold | Captain Mordecai Barrows | Cesar & Ugolín | Chett Englebrick | Clownface | Cooder | Comic Book Guy (Brick Like Me) | Devan & Quenley Woosterfield | Dexter Colt | Dwight Diddlehopper | Frank Grimes, Jr. | Francine Rhenquist | French Chef | Glamorous Godfrey | Howard K. Duff VIII | Ironfist Burns | Jack Crowley | Jack Lassen | Julia | Hell's Satan | Kindergarten Teacher | Larry Kidkill | Lucille Botzcowski | Sparklemon | Lyle Lanley | Les Moore | Jim Hope | Mav & Portia | Molloy | Movementarians | Mr. Dirt | Nigel Bakerbutcher | Officer Krackney | Professor Werner Von Brawn | Rex Banner | Robotic Richard Simmons | Shadow Knight | Stanley DeGroot | The Leader | William Shakespeare | Jay G | Kostas Becker

Video Games
Simpsons Arcade
Hench Dogs | Robot Burns | Mr. Smithers

The Simpsons Game
Matt Groening | Lard Lad | God | King Snorky | Patty & Selma Dragon | Stubborn Ape

The Simpsons: Tapped Out
Mr. Burns | Russ Cargill | Frankie the Squealer | Sven Holly | Evil Homer | Bandits | Count Dracula | Rich Texan | Fernando Vidal | Grampasaurus