The Simpsons’ Best Halloween Episode Isn’t a Treehouse of Horror Special

The spooky Halloween season is the perfect opportunity to go through The Simpsons‘ vast library of Halloween specials, but the best one actually isn’t one of the Treehouse of Horror specials at all. In fact, the best Halloween episode of The Simpsons was the actual first episode of the series set on Halloween that happened much later than fans might have ever expected. The Simpsons is now airing its milestone Season 36 of the long running animated series, and it’s getting ready for its next Treehouse of Horror special in a long line of specials taking the series in wildly different directions.

The Simpsons‘ Treehouse of Horror has become a Halloween mainstay as fans have come to expect three little horror inspired stories every year, and a fun way for The Simpsons to either kick off the Halloween holiday or commemorate it after when they air in November instead. But if you want the best Halloween episode of The Simpsons that’s ever been made, the spookiest and best character study comes in Season 27, Episode 4 with “Halloween of Horror.” It’s the first and so far only episode of The Simpsons to actually be set on Halloween outside of the Treehouse of Horror specials.

What Is Halloween of Horror?

“Halloween of Horror” is unlike the other The Simpsons Halloween specials as it’s set within the universe of the actual series, and actually features the Halloween holiday for the first time in the series’ history. It’s revealed that the entire family is really into the holiday, and even go the extra mile to make sure their house is fully decorated for the occasion. When Homer heads to the local Halloween pop up store for decorations, he ends up ticking off three of the temporary workers there as they lose their jobs when he inadvertently gets them in trouble. The family then heads to Halloween night at Krustyland, and Lisa’s scared out of her mind.

Lisa’s terror is so bad that Homer is forced to take down the house’s Halloween decorations, and on the night of Halloween itself, Homer and Lisa are home alone when the temporary workers show up and try to get their revenge. The episode then turns into a home invasion Horror story as Homer and Lisa not only try and escape from masked assailants, but also bond with one another in a father and daughter story that mirrors some of the best Homer and Lisa bonding stories in episodes past. And on the other side of things, Marge tries her best to make it up to Bart as he’s kind of stuck in the middle of wanting to celebrate the holiday but also wants to be kind to his sister for the moment.

It’s a relatively small story when looking at the scope of The Simpsons‘ horror specials, but it’s the first one that’s allowed to actually use the Halloween holiday to tell a new character story. It shows a new side of Lisa’s past as her panic gets her to revert to a time where she relied on a stuffed tail she named “Tailee,” and Homer is once again on the outside trying to figure out what’s really bothering Lisa. It’s made for a perfect dynamic for the duo that we’ve seen play out in past episodes like Season 9’s “Lost Our Lisa,” Season 10’s “Make Room for Lisa,” or classics like Season 3’s “Lisa the Greek.”

Why Is Halloween of Horror Special?

“Halloween of Horror” was a huge episode when it first premiered back in 2015. The later era seasons of The Simpsons are often ignored by fans who haven’t watched since its “golden era” of the early seasons, and that’s even truer for the mid-twenties seasons as it was before The Simpsons started to experiment in the fun ways that fans are seeing bear fruit now. So “Halloween of Horror,” in retrospect, is the first sign of the kind of changes that would be coming to the long running animated sitcom in the years that followed.

Funny enough, this was actually the same season that started to garner a lot of headlines for its plots like where Homer supposedly cheats on Marge (only for it to be part of an extended fantasy sequence in “Every Man’s Dream”), an episode where Sideshow Bob finally kills Bart in “Treehouse of Horror XXVI,” or the Boyhood experiment episode showing a new future for Bart in “Barthood.” So this was the first real sign that things were beginning to change behind the scenes in The Simpsons, and now we’re finally at the point where big changes are being taken notice of like Homer stopping his choking of Bart for a while.

The Simpsons “Halloween of Horror” might not be a special, but it’s truly special within the scope of the entire animated series. The Simpsons started to make some big changes after this episode came out as it started to reallyform a new era of its humor and voice. It was starting to tease that it wouldn’t be sticking to the old ways of the previous seasons, and it sparked a new evolution. It all started with one of the best episodes of the series in years, and still the best Halloween episode of the series even after all this time. Which might be why The Simpsons has yet to try something like it again.