Villain Overview
Hello, Bart. (Bart and Lisa: Ahhh! Sideshow Bob!)
~ Sideshow Bob's catchphrase and Bart & Lisa's response.

Robert Underdunk Terwilliger Jr, better known as Sideshow Bob, is one of the main antagonists (and sometimes an anti-hero) of the animated TV series The Simpsons. He is Bart Simpson's archenemy.

Sideshow Bob used to be Krusty's sidekick and best friend and co-star of the Krusty the Clown Show, but soon he was so tired of being humiliated by Krusty and wanted him off TV.

He was originally Krusty the Clown's sidekick until he framed Krusty for robbing the Kwik-E-Mart, however he was foiled by Bart Simpson who exposed Bob's scheme. And ever since then Bob has vowed to kill Bart, though on some occasions he has also gone after Krusty.

He is voiced by Kelsey Grammer in his first villain role as he later played Stinky Pete in Toy Story 2, Harold Attinger in Transformers: Age of Extinction, and Hunter in Storks.


Sideshow Bob is a complex character in the series. He is a sadistically obsessed psychopath by trying to kill Bart, yet he is often very smart and sophisticated to 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).

Sideshow Bob enjoys the finer things in life, including reading classical literature and possesses massive. Likely due to his upbringing, he has a passion for theater, knowing Gilbert and Sullivan's H.M.S. Pinafore off 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 his 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 children 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 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).

Other Media

  • Bob also has a brief cameo 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 the audience. Sideshow Bob laughes 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's unknown what happened to him after that, but probably he was then caught and arrested and sent back to jail.


  • Along with Mr. Burns and Kang & Kodos, Sideshow Bob serves as one of the main antagonists of the franchise; however, in The Simpsons Movie, they are all outranked by Russ Cargill.
  • He never made an appearance in The Simpsons Movie. However, Grammer voiced Bob in a deleted scene.
  • Originally, he was set to die in Season 25, but for a strange reason, he didn't die.
  • The episode where Bart first busted Bob marked the first appearance of Simpsons character Kent Brockman.

External links


          The Simpsons Villains

Springfield Republican Party
Birch Barlow | Blue-Haired Lawyer | Lindsey Naegle | Mr. Burns | 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

Environmental Protection Agency
Russ Cargill

Recurring Characters
Agnes Skinner | Artie Ziff | Baby Gerald | Constance Harm | Dolph Starbeam | God | Jebidiah Springfield | Herman Hermann | Itchy | Jessica Lovejoy | Jimbo Jones | Kearney Zzyzwicz | Matt Groening | Nelson Muntz | Patty & Selma Bouvier | Senator Mendoza | Snake Jailbird | Space Mutants | Wainwright Montgomery Burns

Treehouse of Horror
Bart (Fly) | Billy the Kid | Count Burns | Gremlin | Groundskeeper Willie | Homer's Clones | Hugo Simpson II | Jonathan Frink Sr. | Kang and Kodos | Killer Krusty Doll | Killer Toupée | King Snorky | Lard Lad | Muttonchop Murderer | Ned Flanders | Seymour Skinner | The Blob | The Collector | The Devil | The Grand Pumpkin | Witch Marge

Guest Star Characters
Adil Hoxha | Adolf Hitler | Andy Hamilton | Bart Simpson's Creatures | Blue-Eyed Man | Bob Arnold | Captain Mordecai Barrows | Cesar & Ugolín | Clownface | Cooder | Comic Book Guy (Brick Like Me) | Devan & Quenley Woosterfield | Dexter Colt | Francine Rhenquist | Frank Grimes, Jr. | French Chef | Hank Scorpio | Howard K. Duff VIII | Ironfist Burns | Jack Crowley | Jim Hope | Julia | Kindergarten Teacher | Larry Kidkill | Lucille Botzcowski | Lyle Lanley | Mav & Portia | Miss Goodthighs | Molloy | Movementarians | Mr. Dirt | Nigel Bakerbutcher | Officer Krackney | Professor Werner Von Brawn | Rex Banner | Robotic Richard Simmons | Shadow Knight | Simon Cowell | Spud | Stanley DeGroot | Stubborn Ape | The Leader | White Dog | Will Wright