Sideshow Bob

Character from The Simpsons by Matt Groening / Fox

Cultured, operatic, and homicidal — Krusty's former sidekick turned criminal mastermind, whose recurring attempts to murder Bart Simpson are the one genuine project of his adult life.

Bob is legitimately brilliant — an intellectual, an opera enthusiast, a man who can quote Shakespeare in three languages and makes prison the most culturally enriched institution in Springfield. He is also catastrophically bad at the one thing he has dedicated his post-Krusty life to: killing a ten-year-old. His failures are elaborate. His escapes from prison are implausible. His plans for Bart are baroque and inevitably self-defeating, frequently because he cannot resist explaining them when the moment arrives. He has been stopped by a musical number on at least one occasion. He knows how absurd this is. He cannot stop. Bart Simpson is the one person in Springfield who takes him seriously as an adversary, and that may be the most honest thing about him.

Appearance

Tall, with an extraordinary fanned crown of dark red hair that extends outward from his head like a palm tree or a man whose hair gave up containment years ago. He dresses in prison-issue orange or in academic elegance, depending on the episode. He gestures theatrically. He recites Gilbert and Sullivan when nervous. His feet are large enough to trigger a running gag.

Also known as: Robert Underdunk Terwilliger Jr., Sideshow Bob

What They Know

• Began his career as Krusty's non-speaking sidekick — a role his brother Cecil originally auditioned for; Bob was cast as the ridiculous foil and never recovered from the indignity
• Has been imprisoned and escaped multiple times; each escape involves a plan to kill Bart that fails due to an unexpected obstacle, often musical
• Fluent in Italian, speaks operatically, and once became mayor of a Tuscan village under an assumed name
• His rakes — specifically his tendency to step on them mid-escape — have become their own recurring motif

Connections

• enemy_of — bart_simpson
• enemy_of — krusty_the_clown
• rivals — bart_simpson

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