The Simpsons, the longest-running primetime scripted show in television history, has featured a plethora of iconic characters over the years. One of the most beloved and intriguing characters is Sideshow Bob, the former sidekick of Krusty the Clown. Played by the talented Kelsey Grammer, Sideshow Bob has appeared in numerous episodes, leaving an indelible mark on the show.

One of the most iconic episodes featuring Sideshow Bob is "Sideshow Bob's Last Gleaming" (Season 7, Episode 9). In this episode, Bob escapes from prison and takes control of the Springfield Nuclear Power Plant's security systems. He demands that the town watch a classic television show, "The Itchy & Scratchy Show," and threatens to destroy the town if they don't comply.