Robert Underdunk Terwilliger, Jr. Ph. D. 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 University, a member of the Republican Party, and a champion of high culture. He began his career as a sidekick on Krusty the Clowns television show, the plan was foiled by Bart Simpson, and Sideshow Bob was sent to prison. 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, Sideshow Bob shares some personality traits of Grammers character Frasier Crane from the sitcoms Cheers and Frasier, and has been described as Frasier pickled in arsenic. Grammer, who based Bobs 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 2016, Bob has had speaking appearances in 19 episodes and been featured in 13, in addition to his recurring role in the series, Sideshow Bob has made several appearances in other Simpsons media. He appears in the Simpsons Comics, cameos in the 2007 video game The Simpsons Game, Sideshow Bob is also known for his singing voice, several of Grammers performances have been included in The Simpsons musical compilations. The character of Sideshow Bob began his career as the sidekick on Krusty the Clowns television show. The episode Brother from Another Series reveals that Bob only received the job after his younger brother Cecil failed an audition, because Krusty considered Bob to be a perfect comic foil. After repeated instances of abuse, including being shot from a cannon and hit constantly with pies, in Krusty Gets Busted 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, however, Bobs reign is short-lived, Bart Simpson exposes him as the robber, Krusty is released, and Bob is fired and sent to jail. In Black Widower, Bobs first major appearance after framing Krusty, he is released from prison, as part of a scheme to inherit money she has invested in the stock market, Bob attempts to blow Selma up during their honeymoon. Bart again foils the plan and Sideshow Bob returns to prison, after being paroled from prison in Cape Feare, 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 on Terror Lake and he allows a final request, however, and Bart asks to hear Bob sing the entire score of H. M. S. The delaying tactic leads to Bobs third arrest, Bob is released from prison once again in Sideshow Bob Roberts, and runs for Mayor of Springfield as the Republican Party candidate. He defeats Democratic Party incumbent Joe Quimby in a landslide, but Bart and Lisa discover that Bob rigged the election, leading to another incarceration. Bob escapes from prison for the first time in Sideshow Bobs Last Gleaming and he is thwarted when he finds out that the bomb itself is a dud, then kidnaps Bart and flies the Wright Brothers plane in an attempt to kill himself, Bart, and Krusty
Sideshow Bob's brother Cecil was designed to resemble actor David Hyde Pierce, who also played the brother of Grammer's character on the show Frasier.
Image: Kelsey Grammer Cropped
Image: Nancy Cartwright
Sideshow Bob in his brief first appearance in "The Telltale Head". His design was simple compared to later versions and would be refined for his appearance in "Krusty Gets Busted".