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Robert Underdunk Terwilliger, best known as Sideshow Bob is a self-proclaimed genius, member of the Republic Party, champion of high culture, arch-nemesis of Bart and former children's entertainer turned criminal mastermind.

Bob started out as a sideshow for The Krusty the Clown Show but he grew tired of Krusty's abuse. He was sent to prison for framing Krusty for robbing the Kwik-E-Mart. Bart helped clear Krusty, making him Sideshow Bob's greatest enemy.

Bob has tried, and failed, on many occasions to kill Bart. He has been repeatedly sent and released, or escaped, from prison and has always tried to kill Bart and his family. Sideshow Bob tried to put it all behind him and moved to Italy. Here, he got married to Francesca and had a child called Gino. After The Simpsons exposed Bob as a criminal, all three vowed to kill them, including Gino.

Bob has a brother, named Cecil who also hates Bart. His parents, Robert Terwilliger Sr. and Dame Judith Underdunk both were drawn into Bob's hatred for the Simpsons and also helped out in his quest to kill Bart Simpson. Their elaborate plan, however, failed as always.