High Quality Content by WIKIPEDIA articles! Robert Underdunk Terwilliger, better known as 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 is a graduate of 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.