Sideshow Bob (born Robert Underdunk Terwilliger) 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".

Sideshow Bob is one of the most intelligent yet evil characters in The Simpsons universe. After being humiliated by Bart Simpson, Bob has sworn revenge on the entire Simpson family, especially Bart.

Check out Sideshow Bob's best moments! Whether he's trying to kill Bart or singing the entire score of H.M.S. Pinafore, Bob always delivers.

A deep dive into the complex psychology of Sideshow Bob, The Simpsons' most sophisticated villain. From his aristocratic upbringing to his pathological hatred of rakes, we examine what makes Bob tick.