Sideshow Bob Terwilliger (voiced by Kelsey Grammar) used to be Krusty the Klown's sidekick until he tried to frame Krusty for robbing the Kwik-E-Mart. He was then thrown into jail, where he plotted revenge against Bart for years until he got out on parole.

He got out by joining a prison pen pal program and writing to Bart's aunt, Selma, and getting her to fall in love with him. He then married her and tried to kill her. Bart figured out his plan, however, and he was thrown into jail again. He got out again, however, and this time, he was madder than ever.

He actually cornered Bart, but then Bart made his last request: to hear the entire score from the Gilbert and Sullivan musical "The H.M.S. Pinafore." It took Bob and Bart almost three hours to do it, and by the time they were through, they were surrounded by cops.

He got out one last time, and this time he really learned his lesson. However, his brother Nigel (voiced by David Hyde Pierce, who plays Grammar's TV brother, Niles, on NBC's "Frasier") did not. He attempted to frame his brother for the bombing of the Springfield dam and the murder of Bart and Lisa. However, Bob and Bart worked together to foil Nigel's plan.

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