Every ‘Simpsons’ ‘Treehouse of Horror’ Special Ranked

Celebrating the most iconic annual Halloween special on TV, 29 years and counting.
Treehouse Of Horror

18. Treehouse of Horror XXIV (Season 25, October 6, 2013)

This episode could take the cake for its opening alone. Guest co-director Guillermo del Toro’s incorporation of basically the entire horror genre into one opening is absolutely excellent and a fun puzzle to spot out all the references when you have some time. The segments are not bad either. Bart and Lisa being conjoined at the neck after Bart gets decapitated is a pretty frightening thought. And bringing in the Cat in the Hat is an interesting incorporation to a Halloween episode.


17. Treehouse of Horror XXVIII (Season 29, October 22, 2017)

If ever it seemed that The Simpsons was running out of inventive and creative Treehouse of Horror parodies, this episode is here to say they’ve got plenty more we probably haven’t even considered. While not the funniest of the Treehouse episodes, however, this is by far one of the absolute scariest of the series. Maggie with bulging red eyes, a demon voice, and the need for an exorcism just doesn’t feel right. The Coraline tale, however, is gorgeous animated work that really puts into perspective how creepy the real story actually is. That said, it’s always really great when The Simpsons experiments with different animation techniques and forms.


16. Treehouse of Horror XIV (Season 20, November 2, 2008)

Twenty, 50, or 100 years from now, our descendants will probably be looking to various episodes of The Simpsons as pop culture/current events time capsules, and no other Treehouse of Horror episode best exemplifies that more than this one. It references everything from the 2008 presidential election to the peak of Mad Men on TV. It also has a pretty overt commentary on the Transformers franchise through Lisa’s Christmas present, and of course, the show had to at some point parody one of the most famous of Halloween specials of all: It’s the Great Pumpkin Charlie Brown, which is actually the best tale of the whole episode, maybe even one of the best Treehouse of Horror tales ever. Come to think of it, it is pretty strange what we humans do with pumpkins.


15. Treehouse of Horror XVI (Season 17, November 6, 2005)

Treehouse of Horror episodes don’t have to be totally original to be great. Obviously, almost all of them are pulling out references from other horror works. They just have to be able to adequately use those references in a way that feels fresh and fun for the show, and Season 17 is one of the winners on those grounds. A real witch winning a Halloween costume contest and then turning everyone into their costume opens up room for a lot of excellent material that’s clearly present in the episode.


14. Treehouse of Horror XXVI (Season 27, October 25, 2015)

I don’t know about everyone else’s feelings on the matter, but Sideshow Bob has always been a very scary character to me. Even now I find him horrifying. His calm, eloquent voice, as well as his consistent desire to kill Bart, has always sent shivers up my spine. That’s why I was so surprised that he didn’t show up in a Treehouse of Horror episode until now, in the 27th season. This time, however, he actually gets to kill Bart, because of course, this is a Treehouse of Horror episode where death comes by the bucket load. But it’s not all it’s cracked up to be for him. Killing Bart once is apparently not enough. This episode also caused me to notice how, in spite of the extreme amount of gore and death in these specials, there is little to no reaction about them from any of the characters, which helps to make each episode feel fully standalone from the rest of the series, and almost nightmare-like in comparison to the others.


13. Treehouse of Horror XXV (Season 26, October 19, 2014)

I’ll say it here first. I absolutely hate Stanley Kubrick’s A Clockwork Orange. That said, I have to admit that The Simpsons does an excellent parody of it here, turning the most gruesome moments into lighter, comedic bits, but still keeping the eerie shots and essence of the film. Clearly, this is the tale from this episode that is most remembered, but it would be a shame to forget the one before and the one following it. Bart fitting in at school in Hell is something that feels like we would expect to have seen already because it’s a perfect scenario but hadn’t yet. And the ghost of the Simpsons’ past is a fun callback to their earlier animated forms and the show’s evolution since then.


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Natalie Mokry: Film lover and pop culture enthusiast.