Sideshow Bob

Robert Underdunk Terwilliger Jr., PhD, 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 in the episode " The Telltale Head". Bob is a self-proclaimed genius who is a graduate of Yale University and a champion of high culture, including the adoption of a transatlantic accent, similar to that of Grammer's portrayal of Dr. Frasier Crane from the sitcoms ''Cheers'' and ''Frasier''. He began his career as a sidekick on Krusty the Clown's television show, but after enduring constant abuse, Bob framed his employer for armed robbery in " Krusty Gets Busted", only to be foiled by Bart Simpson, and sent to prison. Bob started seeking revenge against Bart while in prison, and the two became feuding arch-enemies.

Bob made his second major appearance in season three's " Black Widower"; the writers echoed the premise of Wile E. Coyote chasing the Road Runner by having Bob unexpectedly insert himself into Bart's life, threatening to disrupt and end it through murder. Starting with that appearance and 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 death and destruction, usually targeted at Bart or, less often, Krusty, though he starts targeting the entire Simpson family in season 17. In season 27, however, during the first segment of " Treehouse of Horror XXVI", entitled "Wanted: Dead, Then Alive", Bob finally gets his wish of killing Bart, commenting that he spent 24 years trying to kill a ten-year-old child; however, he becomes bored with Bart dead, so he brings him back to life so that he can repeatedly kill Bart over and over again.

Despite his villainous deeds, Sideshow Bob shares some personality traits of Grammer's character Frasier Crane, and he has been described as "Frasier pickled in arsenic". Several parallels have been explicitly drawn in ''The Simpsons'' between Bob and Frasier Crane—Bob's brother Cecil and his father were played by David Hyde Pierce and John Mahoney, respectively, echoing the roles they played in ''Frasier''. Grammer, who based Bob's voice on that of actor Ellis Rabb, has been praised for his portrayals of the character. In 2006, he won an Emmy for Outstanding Voice-Over Performance for his work in the episode "The Italian Bob".

As of December 15, 2019, Bob has appeared in more than 40 episodes, had speaking appearances in 23 of these, and been featured as the main character in 14; the most recent of the latter, "Bobby, It's Cold Outside", aired on said date during the 31st season. In addition to his recurring role in the series, Sideshow Bob has made several appearances in other ''Simpsons'' media and is mentioned in several more episodes. He appears in the ''Simpsons Comics'', the 2007 video game '' The Simpsons Game'', and stars as the main antagonist in ''The Simpsons'' Ride at Universal Studios' theme parks. A lover of Gilbert and Sullivan operettas, Sideshow Bob is also known for his singing voice; several of Grammer's performances have been included in ''The Simpsons'' musical compilations.

Appearances

On ''The Simpsons''

The character of Sideshow Bob began his career as the non-speaking sidekick on Krusty the Clown's television show. Bob first appears in " The Telltale Head" (season 1, 1990). In the episode, he and Krusty plan a big event for whoever knows information of who captured the head of Jeremiah Springfield's statue, and joins in on the town mob when it is discovered that Bart Simpson took it. However, after repeated instances of abuse, including being shot from a cannon and hit constantly with pies, the Yale-educated Bob became angry at Krusty and resentful of the clown's success. In " Krusty Gets Busted" (season 1, 1990), Bob disguised himself as Krusty and framed him for armed robbery of the Kwik-E-Mart. After Krusty is arrested, Bob takes control of the show, introducing children to elements of high culture. However, Bob's reign is short-lived; Bart exposes him as the robber, Krusty is released, and Bob is fired and sent to jail.

In " Black Widower" ( season 3, 1992), Bob's first major appearance after framing Krusty, he is released from prison and marries Bart's aunt Selma Bouvier as part of a scheme to inherit money she has invested in the stock market. Bob attempts to blow Selma up during their honeymoon, but Bart again foils the plan and Sideshow Bob returns to prison.

After being paroled from prison in "Cape Feare" (season 5, 1993), Bob targets Bart directly, threatening him repeatedly and forcing the Simpsons into hiding as part of the Witness Relocation Program. Bob follows them to their hideout, a houseboat