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Sideshow Bob

Sideshow Bob is a recurring fictional character in the animated television series *The Simpsons*.

By Ethan Anderson| Reviewed by Olivia Bennett, Standards & Fact-Checking Lead| Updated July 26, 2026|2 min read| Fact-checked

Sideshow Bob is a recurring fictional character in the animated television series *The Simpsons*. He is Dr. Robert Underdunk Terwilliger, voiced by Kelsey Grammer, and is known as a cultured criminal mastermind and Bart Simpson's enemy. He first appeared in the episode "The Telltale Head" and later became one of the show's most recognizable antagonists. The character is widely known to Canadian viewers through the show's broadcast and syndication in Canada.

Character overview

Sideshow Bob is a fictional character from *The Simpsons* who is usually portrayed as an erudite but villainous figure. He is known for his cultured speech, grandiose self-image, and repeated schemes against Bart Simpson. His full name is Dr. Robert Underdunk Terwilliger, and he is a self-proclaimed genius with a passion for high culture.

Role in The Simpsons

Sideshow Bob originally worked as Krusty the Clown's sidekick before turning to crime. Over time, he became a recurring antagonist whose storylines often involve revenge and criminal plotting. His schemes are frequently thwarted by Bart Simpson's interference.

Voice and portrayal

Sideshow Bob is voiced by Kelsey Grammer, whose performance helped define the character's distinctive personality and speech. The role became one of Grammer's best-known voice performances.

Character traits

Bob is depicted as a self-proclaimed intellectual with a preference for high culture and a transatlantic accent. He is also known for his dramatic hair, large feet, and elaborate schemes.

Key facts

  • Sideshow Bob is a recurring antagonist in *The Simpsons*.
  • He is voiced by Kelsey Grammer.
  • His character's real name is Dr. Robert Underdunk Terwilliger.
  • He first appeared in "The Telltale Head".
  • He was originally Krusty the Clown's sidekick before becoming a criminal.
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Canadian context

Sideshow Bob is widely known to Canadian viewers through *The Simpsons*, which has long been broadcast and syndicated in Canada.

Frequently asked questions

Who is Sideshow Bob?
Sideshow Bob is a fictional character from *The Simpsons*, best known as a recurring villain and Bart Simpson's enemy.
What is Sideshow Bob's real name?
His real name is Dr. Robert Underdunk Terwilliger.
Who voices Sideshow Bob?
Sideshow Bob is voiced by Kelsey Grammer.
What was Sideshow Bob's original job?
He originally worked as Krusty the Clown's sidekick before turning to crime.
When did Sideshow Bob first appear?
He first appeared in the *The Simpsons* episode "The Telltale Head".

References

  1. Wikipediahttps://en.wikipedia.org/wiki/Sideshow_Bob
    Supports: Real name, role in The Simpsons, voice actor, first appearance, recurring antagonist status
  2. Britannicahttps://www.britannica.com/topic/Sideshow-Bob
    Supports: Character identification, voice actor, role as a recurring Simpsons character
  3. Dictionary.comhttps://www.dictionary.com/culture/fictional-characters/sideshow-bob
    Supports: Character description, first appearance, role as Krusty’s sidekick, Bart rivalry, distinctive hair and personality