5. Treehouse Of Horror III
Kicking off the top five is the third entry in the Treehouse of Horror saga which exemplifies everything you love about both the Simpsons and this spooky holiday. One of only four specials to focus on a theme of scary storytelling, Treehouse of Horror III sees the Simpsons and friends gather on a stormy Halloween night for a party filled with fun and terror. Among the best of the costumes are Bart as Alex DeLarge, Martin as Calliope, and Homer and Marge's duo of Caesar and Cleopatra. While the second segment "King Homer" misses the mark when it comes to Halloween, it's still decent enough to deserve some recognition. The remaining two segments are a definite tie with each offering up some hilarious scares. "Clown Without Pity" parodies the many horror tales of evil dolls with Krusty the Clown as the eponymous killer. "Dial 'Z' for Zombie" made the walking dead cool before AMC got a hold of the concept. Many will argue that the earlier episodes of Treehouse of Horror are among the best and they'd be mostly correct. Treehouse of Horror III features everything that made you fall in love with these specials in the first place and was a major player in pushing the series forward.