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Sideshow Bob is a recurring character on The Simpsons. Since season three's "Black Widower" (1992), the writers have echoed the premise of Wile E. Coyote chasing the Road Runner from the 1949–1966 Looney Tunes cartoons by having Bob unexpectedly insert himself into Bart's life and attempt to kill him. Executive producer Al Jean has compared Bob's character to that of Wile E. Coyote, noting that both are intelligent, yet always foiled by what they perceive as an inferior intellect. The scene in which Bob is stomped on by multiple elephants and bounced right back up is a reference to the Wile E. Coyote character.

In Planet Simpson, author Chris Turner writes that Bob is built into a highbrow snob and conservative Republican so that the writers can continually hit him with a rake and bring him down. He represents high culture while Krusty, one of his archenemies, represents low culture, and Bart, stuck in between, always wins out. In the book Leaving Springfield, David L. G. Arnold comments that Bart is a product of a "mass-culture upbringing" and thus is Bob's enemy.

Bob's intelligence serves him in many ways. During this episode, for example, the parole board asks Bob why he has a tattoo that says "Die Bart, Die". Bob replies that it is German for "The Bart, The"; members of the board are impressed by his reasoning. Believing that "nobody who speaks German could be an evil man", they release him. However, his love of high culture is sometimes used against him. In the same episode, Bob agrees to perform the operetta H.M.S. Pinafore in its entirety as a last request for Bart. The tactic stalls Bob long enough for the police to arrest him.