Since its second season, The Simpsons has released its annual Halloween special Treehouse of Horror, and the best of these horror movie-parodying anthologies rank among the best episodes the show has produced. Each episode involves three tales of satirical terror inspired by horror, science fiction, and the supernatural. Over the decades, the residents of Springfield have morphed into recognizable monsters, been tempted by the devil, and parodied pop culture's favorite scary stories. Beyond mere homage, these segments innovate within the genres they mimic, providing fans with a fresh yet frighteningly fun perspective on the tropes the world knows and fears.

The Treehouse of Horror segments gleefully abandon normal continuity in The Simpsons, killing off characters at random. In many, the characters also break the fourth wall with introductions and warnings, which pays homage to classic anthology series like The Twilight Zone. This narrative device serves as both a tribute and a technique for the writers to be as creative as they like without worrying about adhering to the show's verisimilitude. However, over 30 specials later, the earliest Halloween specials are still considered superior, and the best Treehouse of Horror episodes stand out despite the specials being consistently high-quality.

20 Treehouse Of Horror XXI (2010)

The Simpsons Takes On Jumanji And Twilight

"Treehouse of Horror XXI" delivers a triad of tales that blend horror and humor with The Simpsons' signature style. The episode parodies the movie Jumanji with a cursed board game that unleashes real perils, while the second segment humorously tackles Twilight, introducing a lovelorn vampire. The final act is an homage to Dead Calm, where the Simpsons face off against a mariner with murderous intent.

Its pop culture riffing is sharp, and the Twilight parody stands out for cleverly lampooning the vampire craze of the 2000s, capturing the essence of what makes these episodes fan-favorite satire with a Simpsons twist. It is especially elevated by the clever casting of Daniel Radcliffe as the vampire boy who develops a romantic connection with Lisa. The episode does highlight some of the unevenness of the later Halloween specials, but it also features some writing that would be at home in the best seasons of the show.

19 Treehouse Of Horror XVI (2005)

Mr Burn's Goes Hunting And Bart's Replaced By A.I.

In "Treehouse of Horror XVI," the show presents a brilliant blend of classic and contemporary. The episode opens with a "B.I.: Bartificial Intelligence" segment, exploring artificial intelligence with a Simpsonian spin. This is followed by "Survival of the Fattest," a macabre take on reality television where Mr. Burns hunts Springfield's men for sport.

"I've Grown a Costume on Your Face" displays the show's whimsical side as a witch turns everyone into their Halloween costumes. Its standout feature is the clever satire on the then-emerging reality TV phenomenon, offering both a critique of society and a plethora of laughs. It also feels like a throwback to an era in the show in which the Treehouse of Horror segments were not overly concerned with being parodies of recognizable movies. This clever Halloween tale fits with the spooky season while also delivering big laughs.

18 Treehouse Of Horror XXIII (2012)

Black Holes And Time Travel Make For A Great Simpsons Halloween Episode

The 23rd installment in the "Treehouse of Horror" series makes a remarkable splash with its segments. The episode kicks off with an apocalyptic vision in "The Greatest Story Ever Holed," which sees Springfield succumbing to a black hole. "UNnormal Activity" parodies the found footage horror genre, and the final story, "Bart & Homer's Excellent Adventure," riffs on time-travel tropes. What makes this episode great is its contemporary take on modern fears — from black holes to surveillance — while maintaining the show's characteristic levity and irreverence.

There are a lot of fun gags seeing the Simpson family starring in their own found footage movie.

The episode is a testament to the series' ability to remain topical and engaging even after two decades. There are a lot of fun gags seeing the Simpson family starring in their own found footage movie. However, the best segment is the first one, once again proving a direct parody of a movie is not always necessary. The fun premise of a black hole gradually consuming Springfield allows for those fun moments of the show's large ensemble to get involved.

17 Treehouse Of Horror XIX (2008)

A Heavy Dose Of Social Commentary Makes This Halloween Special Stand Out

"Treehouse of Horror XIX" strikes with its usual wit and a touch of the macabre. The episode takes a stab at the Transformers movie series with "Untitled Robot Parody." The episode becomes more insightful with "How to Get Ahead in Dead-vertising," skewering the world of advertising by killing celebrities to use their likenesses for free, which is an eerily prescient segment given current concerns about studios using A.I. Lastly, "It's the Grand Pumpkin, Milhouse" satirizes the classic Peanuts Halloween special, giving it a dark twist.

The keen social commentary wrapped in fantastical horror-comedy makes "Treehouse of Horror XIX" particularly memorable. The first two segments set the episode up to be a rather weak entry in the Treehouse of Horror tradition. The Transformers parody seems uninspired while the second story feels like an excuse to include impressions of celebrities. However, the Charlie Brown story saves the show with a fitting Halloween-centric story with a fun twist on the classic cartoon.

16 Treehouse Of Horror XX (2009)

The 20th Treehouse Of Horror Marks An Important Milestone

Marking the 20th Anniversary of the "Treehouse of Horror" specials, this episode combines homage with innovation. The opening act, "Dial 'M' for Murder or Press '#' to Return to Main Menu," takes a swing at Hitchcockian tropes with a twist-filled black-and-white segment. In "Don't Have a Cow, Mankind," a spoof of zombie films, Krusty Burger's new burger turns the town into a horde of zombies. The final tale, "There's No Business Like Moe Business," is a musical that cleverly unfolds on stage.

What makes this episode stand out is the theatrical flair and classic horror homage, encapsulating the creativity that has kept the series fresh over the years. The musical segment makes for a unique format for the story to unfold while the zombie story proves that even material that the show has already used can be revisited in worthwhile ways.

15 Treehouse of Horror XV (2004)

Ned Flanders Gains Prescience And Lisa Stalks A Killer Across 19th Century London

One of many Stephen King adaptations on the show, The Simpsons tackles The Dead Zone in season 16. The hilarious story finds Ned Flanders experiencing visions of the future, including one in which Homer causes a devastating disaster — which is not very surprising. One of the episode's other stories includes a murder mystery set in the early 1900s with Lisa as a detective tracking a Jack the Ripper-like killer through the streets of London. There is also a fun sci-fi adventure in which Maggie is shrunk down and accidentally swallowed by Mr. Burns.

This Treehouse of Horror episode feels like the show once again embracing the freedom of these Halloween specials. It takes advantage of being able to tell some very different and inventive stories instead of just churning out another spoof. From period mysteries to sci-fi adventures, it makes for a well-rounded episode.

14 Treehouse of Horror XII (2001)

Pierce Brosnan's Cameo As A Homicidal A.I. Homer

Another great Simpsons guest star playing themselves is Pierce Brosnan, who appears in a segment as the celebrity A.I. voice for the family's smart home. However, things get weird when the supercomputer develops a fixation on Marge. Other stories include Homer getting a curse put on him that punishes those around him, as well as a Harry Potter-inspired adventure with Lisa and Bart at a magic school where Bart takes extreme measures to beat his top-student sister.

While the earlier Treehouse of Horror episodes didn't lean as much into the guest stars, Brosnan's vocal performance elevates the final story.

The Harry Potter story is also a lot of fun as it avoids the problem with a lot of the later parody segments in that it is willing to be its own thing. It is another varied and funny example of the creativity of these episodes.

13 Treehouse of Horror XIV (2003)

Home Becomes The Grim Reaper

While Homer Simpson has had a number of jobs over the course of the series, this episode finds Homer taking up the mantle of the Grim Reaper himself. As with all of his responsibilities, Homer doesn't take the position as seriously as he should. There is also a fun misadventure with Bart and Millhouse as they get their hands on a watch that can stop time. Professor Frink takes center stage in another story as he seeks to raise his father from the dead.

In a fun bit of The Simpsons casting, Frink's father is voiced by Jerry Lewis, whom the animated character is based on. However, the episode shows the signs of the Treehouse of Horror episodes beginning to lose their focus. While the jokes were still laugh-out-loud funny, the stories had become less interesting and clever.

12 Treehouse of Horror XI (2000)

Humanity Is Ousted By Dolphins

Homer has met a grisly end in many of these episodes, but season 12 sees him having to contend with the afterlife. After dying from eating broccoli, Homer is told he must complete one good deed in order to get into heaven — but it is not as easy for him as it sounds. There is also a retelling of Hansel and Gretel in which Bart and Lisa are confronted with a witch living in a gingerbread house. But the episode's highlight is a hilarious spoof of animal attack horror movies with super-intelligent dolphins taking revenge on humanity.

The gory mayhem of the dolphin attacks makes for an ideal cap to the episode. It is another segment that goes very broad with its storytelling and delivers a hilariously dark ending with humanity forced to live on the ocean after being defeated by the dolphins. As Homer points out, the dolphins "just wanted it more."

11 Treehouse of Horror XIII (2002)

The Simpsons Unleashes Multiple Homers

Homer Simpson can be destructive enough on his own, and this Simpsons Halloween special imagines the trouble that is caused when there are endless duplicates of him. That is the dilemma in the first segment of this season 14 episode, as Homer clones himself using a magic hammock, and it's expectedly hilarious. There is also a story in which the people of Springfield decide to give up their firearms with unexpected consequences as an army of gun-toting zombies descends on the town. Lastly, there is a creepy tale of Dr. Hibbert owning an island where he turns people into animals.

The episode takes segments that could feel like they would be obvious and fall into the decline of the show's writing in this era. However, the episode is a bright spot in season 14, with the segments embracing the wackiness and weirdness of the Halloween episodes. It makes for a wild and fun journey with the genuinely creepy segment spoofing the Island of Doctor Moreau as the highlight.