Episodes With Sideshow Bob Updated Jun 2026

. Sideshow Bob Roberts (S6, E5): Bob enters politics, running for Mayor of Springfield as a "law and order" Republican. Though he wins in a landslide, Lisa and Bart expose that he rigged the election using the names of dead voters and pets. Show more Shifting Roles and Redemption Arcs Brother from Another Series (S8, E16): Bob is released into the care of his brother, Cecil (voiced by David Hyde Pierce). In a twist, Bob becomes the hero, helping Bart and Lisa stop Cecil’s plot to blow up a dam. The Italian Bob (S17, E8): Bob flees to Italy, becomes a mayor, and starts a family. His past is eventually revealed by a drunken Lisa, leading his entire family to join him in a vendetta against the Simpsons. The Man Who Grew Too Much (S25, E13): Bob alters his own DNA to gain superhuman abilities, including sonar and grasshopper-like leaping. He eventually attempts suicide out of remorse, only to survive because he gave himself gills. YouTube +3 Show more Alternative Realities In the non-canonical Treehouse of Horror XXVI (2015), Bob finally succeeds in killing Bart. However, he finds life meaningless without his rival and uses a reanimation machine to repeatedly kill and resurrect Bart just for the thrill. Villains Wiki +1 Bob’s character has evolved from a simple criminal into a tragic, self-aware figure who occasionally assists the family, as seen in The Great Louse Detective (S14, E6) , where he helps find Homer’s attempted killer. YouTube +1 Are you interested in a deeper look at the

Bored with the mundane life of a minimum-security prison, Bob escapes to take over a local air show. His demand? All television broadcasts must cease. It’s a plot that plays perfectly into Bob’s elitist personality—he hates the lowbrow entertainment that keeps the masses docile. episodes with sideshow bob

In the sprawling, yellow-skinned universe of The Simpsons , most antagonists are driven by petty greed, laziness, or simple malice. But Sideshow Bob (voiced with Shakespearean relish by Kelsey Grammer) is different. He is the cultured, vengeful, and unhinged foil to Bart Simpson—a man whose genius is matched only by his homicidal obsession with a ten-year-old boy. Show more Shifting Roles and Redemption Arcs Brother

While Snake Jailbird is a common criminal and Mr. Burns is a corporate tyrant, Robert Underdunk Terwilliger Jr. is something else entirely. He is a man of culture, a classically trained actor, a Harvard graduate, and a man with a grudge so potent it has fueled some of the funniest—and smartest—episodes in the show’s history. His past is eventually revealed by a drunken