‘The Simpsons’: Best Halloween Episodes of All Time

The Simpsons
The Simpsons | FOX

The Simpsons‘ legacy as a television pioneer is secure beyond a shadow of a doubt. After all, the show is among the longest-running sitcoms and animated series ever made, with 600 episodes produced since its debut in 1989. Fans may be a bit divided over whether or not the show has overstayed its welcome, but there’s something reassuring in knowing that the yellow-skinned residents of Springfield are there every week to create mischief and go on an endless series of misadventures.

Even if we never get a sequel to the 2007 big-screen hit The Simpsons Movie, Homer, Marge, Bart, Lisa, and Maggie have at least fulfilled the promise of their annual Halloween specials. Over the years, many shows have attempted to capitalize on the ghoulish holiday with spooky traditions (Roseanne comes to mind as a particularly successful example), but few can compare with The Simpsons‘ devotion to parodying all things horror in its Treehouse of Horror episodes. To date, the show has aired 27 installments in the fan-favorite series of Halloween-themed episodes, starting with Season 2. Let’s take a look at some of the best ones to come out over the show’s first 28 seasons.

10. ‘Treehouse of Horror IX’

Kicking off our list is this ninth installment, which may very well be best remembered for its epic couch gag. The show itself offers lots to enjoy as well. Its first segment deals with a hair transplant that sees Homer possessed by the spirit of a criminal, followed by a story featuring Bart and Lisa trapped within The Itchy & Scratchy Show. However, it’s the final segment — in which Marge reveals the shocking truth of Maggie’s paternity — that may be the most notable.

9. ‘Treehouse of Horror II’

The second Treehouse of Horror is one of the only ones to have a conscious theme running from one segment to the next. This entry is, of course, broken down into the traditional three-segment structure, but each one is essentially based on a particular character’s nightmare. It’s also the first to feature “scary-name” variations of the cast and crew in the credits.

8. ‘Treehouse of Horror VIII’

Parodies of The Omega Man, The Fly, and The Scarlet Letter make up this eighth entry in the series. Just another example of the show’s knack for weaving together absurdist comedy with pop cultural landmarks, the episode is also notable for being the last one Brad Bird worked on before leaving the show to direct The Iron Giant.

7. ‘Treehouse of Horror XII’

Thanks to the World Series, this entry didn’t air until early November, but it still remains a favorite, thanks in part to the Harry Potter parody “Wiz Kids.” Pierce Brosnan and Matthew Perry also guest star, and the episode intriguingly relied more on sci-fi and fantasy references as opposed to the traditional horror ones used in previous years.

6. ‘Treehouse of Horror VII’

The Simpsons got political in this installment, centering an entire segment on the upcoming presidential showdown between Bill Clinton and Bob Dole. Entitled “Citizen Kang,” this segment is often considered to be among the best in the Treehouse of Horror series and a personal favorite for series creator, Matt Groening. Phil Hartman even reprised his Saturday Night Live role as Clinton.

5. ‘Treehouse of Horror’


The one that started it all. Since this inaugural entry, the show’s parody of Edgar Allen Poe’s The Raven still stands among the best-known segments the show has ever produced. This episode also marks the first-ever appearance of drooling aliens Kang and Kodos. Clearly, the show’s creative team saw the potential that seeped from every frame, as Treehouse of Horror is running strong nearly 30 years later.

4. ‘Treehouse of Horror III’

The first few installments of The Simpsons undoubtedly yielded some of the best Halloween specials. Case in point: This episode takes on everything from zombies to Alfred Hitchcock Presents, proving that the show was uniquely equipped to tackle virtually any spooky element it wanted. Both “Dial Z for Zombies” and “Clown Without Pity” are considered among the best segments ever.

3. ‘Treehouse of Horror VI’

The show has never shied away from taking creative chances. So this episode’s computer-animated segment — in which Homer winds up trapped in another dimension — was a particularly memorable experiment. Moreover, its parody of A Nightmare on Elm Street raised the bar for the show’s ability to tackle even the most iconic horror franchises and soar as a result.

2. ‘Treehouse of Horror IV’

Casting the ultra-religious Ned Flanders as the Devil is precisely the ironic decision The Simpsons would make. So “The Devil and Homer Simpson” is predictably hilarious. That’s only the first segment, however, and the subsequent parodies of The Twilight Zone and Bram Stoker’s Dracula make this one of the most consistently outstanding Halloween episodes in the show’s history.

1. ‘Treehouse of Horror V’

Anyone who has seen this incomparable episode shouldn’t be too surprised to see it top our list. The spot-on parody of The Shining alone would make it one of the best ever, but luckily “Nightmare Cafeteria” and “Time and Punishment” — in which Homer meddles with time travel — are up to the challenge. This is pure gold all the way around and has yet to be topped.

Follow Robert Yaniz Jr. on Twitter @CrookedTable.

Check out The Cheat Sheet on Facebook!