The Devil and Homer Simpson (Season 5, “Treehouse of Horror IV”)
Technically this is all unranked, but if I were ranking them, “The Devil and Homer Simpson” would likely be at the top. Homer selling his soul to the devil—who knows Bart personally and looks like Flanders—is a great concept, and the writers perfectly wring out every drop of humor. I quote this segment more often than I care to admit and the bit with Homer chomping away on endless donuts in Hell is one of the funniest visual gags in the show’s history. All that, plus a heartwarming ending and a wild twist with a killer final joke! What a segment!
