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Enough of Krusty's torment, Bob framed Krusty 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.After being paroled from prison, Bob targeted Bart directly, threatening him repeatedly and forced the Simpsons to move to Terror Lake as part of the Witness Relocation Program. After being released, he ran for Mayor of Springfield on a Republican Party ticket.Bob followed them to their houseboat and, after subduing the family, prepared to kill Bart. He defeated liberal incumbent Joe Quimby in a landslide, and used his power as mayor to propose the demolition of the Simpsons house to make way for an Expressway, and sent Bart back to Kindergarten.Bob took part in a prisoner dating service, and went into a relationship with Selma Bouvier, the aunt of Bart.After he was released from prison, he proposed to and married Selma, despite Bart's protests.He allows a final request, however, and Bart asks to hear the entire score of H. Bart and Lisa later discover that Bob rigged the election, leading to another incarceration.
However, Bob's reign is short-lived; Bart Simpson exposes the plan, Krusty is released, and Bob is sent to jail, but not before swearing vengeance on Bart.During his time in prison, Bob won an Emmy for his role on The Krusty the Clown Show, but his award was confiscated by the prison guards.Robert "Bob" Underdunk Terwilliger, Jr., better known by his stage name, Sideshow Bob, is a self-proclaimed genius, member of the Republican Party, champion of high culture, Bart Simpson's archnemesis and former children's entertainer turned criminal mastermind.Little is known of Bob's early life, however his career as a children's entertainer started as the non-speaking sidekick on Krusty the Clown's television show.
As part of a scheme to inherit money she has invested in the stock market, Bob attempted to blow Selma up during their honeymoon.However, Bart again foiled the plan and Sideshow Bob returns to prison, exclaiming that as soon as the Democrats were back in office, he and all his criminal buddies would be back on the streets. Bob was released from prison once again after conservative commentator Birch Barlow convinced the public that Bob was a political prisoner.