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10) Lisa's Nightmare aka Monkey’s Paw (Treehouse of Horror II)

One of the many aspects of The Simpsons that stole my heart in the early days was the show’s innate ability to bring stories full circle and even half a circle beyond. No complete episode better demonstrates this behavior than this segment, which begins with The Simpsons marveling at their fortune over a magical, wish providing Monkey’s Paw. How does the family spend three of their four wishes? The thoughtless requests are a pacifier, fortune/fame and a slightly dry turkey sandwich.

The clever twist is that the one unselfish request, the one obviously made by Lisa, at least temporarily enslaves humanity. Lisa’s benevolence backfiring has become a recurring theme in Treehouse of Horror episodes, but this is the one that is handled most capably. In requesting world peace, she breaks an unknown détente with everyone’s least favorite siblings from Rigel VII, allowing them to conquer Earth, even though their primary weapon is a giant slingshot. Why didn’t Bart think of that? We’ll never know.

The end result is that The Simpsons dispose of the Monkey’s Paw, thereby unintentionally allowing Flanders to liberate his fellow Springfieldians thanks in large part to boards with nails in them. And by the end of the segment, Homer has gone from completely ignorant of the Monkey’s Paw to a victim of buyer’s remorse for said object to a jealous witness of Flanders’ exponentially better usage of the Monkey’s Paw. Out of all the Twilight Zone parodies, this is the satire that is purest. As an aside, I love the idea that one day in the future when a Simpsons Movie sequel is made, Hank Scorpio’s master plan is revealed…and he has created a Board with a Nail in It so big it will destroy us all.

9) The Devil and Homer Simpson (Treehouse of Horror IV)

What always makes me come back to this episode is the sublime decision to out Flanders as the Devil. As he says, it is always the one we least expect and that premise alone leads to a lot of great jokes. There are several throwaway gags such as “Hot pen!” and “I don’t understand. James Coco went mad in 15 minutes”, but my favorite is the random insertion of the Broad Street Bullies, the 1976 Philadelphia Flyers, as members of the jury. The fact that there is no rhyme or reason to it makes the choice all the funnier. This is the most romantic of the Treehouse of Horror episodes, which on its own is enough to set the episode apart, and I always love the episodes where Homer demonstrates enough romance to explain why Marge stays with him despite his innumerable character flaws.

8) The Shinning (Treehouse of Horror V)

For a couple of years, I had my computer’s startup sound file as “GO CRAZY? DON’T MIND IF I DO!!!” I liked the fact that every reboot put a smile on my face in this regard thanks to the perfect enunciation of Dan Castellaneta. I have complete confidence that there is universal consent among the people reading this that The Shinning is clearly one of the ten best segments of Treehouse of Horror. The question would be why I have it so low. The realistic answer is that I have been able to quote every line of its dialogue since 1994, making it feel a bit stale. There was a period of several years where this would have been my easy choice for first place, but it has become oversaturated in the interim. This probably makes your urge to kill rise, and I respect that.

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