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Robert Underdunk Terwilliger, better known by his stage name Sideshow Bob, is a recurring character in the animated television series The Simpsons. He is voiced by Kelsey Grammer. Sideshow Bob has been described as "Frasier pickled in arsenic", which is appropriate as Kelsey Grammer played Frasier Crane on the series Frasier. In 2006, Grammer won an Emmy for Outstanding Voice-Over Performance for his portrayal of Bob in the episode "The Italian Bob." Sideshow Bob was originally the sidekick on Krusty the Clown's television show, but Krusty's continuous abuse led to Bob framing him for armed robbery. Krusty was arrested and Bart Simpson discovered that Bob was behind the crime, leading to Bob's arrest. Since then he has been a villainous homicidal maniac, as well as Bart's mortal enemy, and as a result he has tried to kill Bart on several occasions. Bob has been featured in nine episodes, with another one set to air during the nineteenth season.

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 Frasier actor Kelsey Grammer. Grammer used his impression of Ellis Rabb, a man that Grammer had once worked for, 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, he was actually named after the character Dr. Terwilliker from the film The 5,000 Fingers of Dr. T.