1688. Sideshow Bob

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 and first appeared briefly in the episode "The Telltale Head". Bob is a self-proclaimed genius who attended Yale, a member of the Republican Party, and a champion of high culture. He began his career as a sidekick on Krusty the Clown's television show, but after enduring constant abuse, Bob attempted to frame his employer for armed robbery in "Krusty Gets Busted". The plan was foiled by Bart Simpson, and Sideshow Bob was sent to prison. Bob made his second major appearance in season three's "Black Widower"; the writers echoed the premise of the Coyote chasing the Road Runner by having Bob unexpectedly insert himself into Bart's life and attempt to kill him. In each appearance thereafter, Bob has assumed the role on The Simpsons of an evil genius. Episodes in which he is a central character typically involve Sideshow Bob being released from prison and executing an elaborate revenge plan, usually foiled by Bart and Lisa. His plans often involve murder and destruction, usually targeted at Bart or, less often, Krusty, though these plans often involve targeting the entire Simpson family. In "Funeral for a Fiend" it was hinted that through years of failed attempts, Sideshow Bob has become insane.