Sideshow Bob is one of The Simpsons ’ most iconic recurring villains. A genius former sidekick to Krusty the Clown, Bob frames his rival and tries to kill Bart Simpson in almost every appearance. His appearances are famous for Shakespearean dialogue, intricate plots, and the "rake stepping" gag.

Kelsey Grammer's portrayal of Sideshow Bob has been widely praised, earning him multiple Emmy nominations. His character's legacy extends beyond The Simpsons, with Sideshow Bob becoming a cultural icon.