10. The Island of Dr. Hibbert (Treehouse of Horror XIII, 2002)
In one of the first episodes centered around Dr. Hibbert, it shows the doctor inviting the residents of Springfield to his mysterious island resort, where they are transformed into animals. The segment is a parody of HG Wells' popular novel The Island of Dr. Moreau, that sees a similarly insane doctor turning animals into human-like creatures. This segment is particularly worth it, as its a lot of fun to see all our favorite characters in animal form. It may not reach the heights the classic segments from years before did, but it is certainly one of the show's better segments.
09. Its the Grand Pumpkin, Milhouse (Treehouse of Horror XIX, 2008)
One of the few latter day Treehouse of Horror episodes that actually stands out. In both a loving tribute and blatant parody of the classic Charlie Brown Halloween special, the segment concentrates on a depressed Milhouse, and how the Grand Pumpkin comes to life to make everything better. Of course, this is The Simpsons, and there are healthy doses of satire thrown in there, and along with the exquisite animation, it remains one of the best segments from the later years of the show
08. Homer³ (Treehouse of Horror VI, 1995)
Today, it has become so common for animated movies to be made with CGI. However, in 1995, The Simpsons made television history in their Halloween special, where they did something very rarely done on television at that point - made an episode with CGI imagery. The episode sees Homer hiding from his nasty sisters-in-law Patty and Selma and finding a wormhole that thrusts him into a surreal region where mathematical equations and scientific theories decorate the air. Homer is transformed into a three-dimensional entity. Looking at the episode now, nearly twenty years later, the animation does seem basic and pretty mediocre, but when the episode was produced, it was groundbreaking technology. The episode is worth it for any science or math boffins, as there are plenty of references hiding in the background of every frame.
07. The Raven (Treehouse of Horror, 1990)
An almost word-for-word interpretation of the Edgar Allan Poe short story, where Homer plays the protagonist of the story, and Bart plays the pesky and mysterious raven. It may not be funny, but it was beautifully animated, and boasts heavenly narration from James Earl Jones.
06. Dial Z for Zombies (Treehouse of Horror III, 1992)
A lesson to The Walking Dead - The Simpsons did the zombie apocalypse first. In one of the show's weirdest and most terrifying segments, Springfield is overtaken by zombies, and the Simpsons are the only hope for the town's survival. It may be very tame compared to modern zombie pop culture, but it is still brilliantly satirical and worth it for all the classic one liners, including Homer's reaction to shooting Ned Flanders.
05. The Thing and I (Treehouse of Horror VII, 1996)
The best part of the Treehouse of Horror episodes is that they are considered non-canon to the show, so writers and animators have carte blanche to do whatever they want with the characters, including killing them off and introducing all sorts of monsters into Springfield. In "The Thing and I," Bart discovers that he actually has a twin brother, Hugo, who lives in the attic and is fed on fish heads by Homer. When he escapes, the family frantically searches for him, as he is apparently the evil twin. However, when they eventually find him, it is revealed that maybe the evil twin isn't actually Hugo. It is a very simple premise, but a brilliantly twisted story. Hugo has gone on to become an iconic Treehouse of Horror character, and many fans anxiously want him to return at some point.
04. Time and Punishment (Treehouse of Horror V, 1994)
In one of the most mind-bending episodes of The Simpsons, Homer attempts to fix a broken toaster, but he accidentally turns it into a time machine, which transports him to the past. He realizes the tiniest changes he makes may change the future, and of course he makes the smallest errors - swatting a mosquito, stepping on a fish, sneezing and infecting the dinosaurs--all if which result in various alternative futures, including one where Ned Flanders rules a lobotomized humanity and where it rains donuts.
03. Nightmare on Evergreen Terrace (Treehouse of Horror VI, 1995)
This segment actually gave me nightmares. It is a parody of the highly successful and iconic Nightmare on Elm Street film series, with Groundskeeper Willie filling in for Freddie Krueger. Wearing the same stripped sweater and fedora, and wielding a rake instead of claws, Willie terrorizes the children of Springfield before the segment takes a terrifying and disturbing turn. It is definitely one of the most terrifying segments the show has ever produced.
02. The Devil and Homer Simpson (Treehouse of Horror IV, 1993)
The idea of selling your soul to The Devil for some dream or goal is a common cliche in pop culture, and The Simpsons is no exception. However, they managed to put their own original spin on it, turning the well-worn trope into something comedically brilliant. Homer desperately wants a donut, and thus oaths to sell his soul to Satan for a donut. Of course, Ol' Scratch is played by the least obvious candidate - the pious Ned Flanders. When Homer refuses to give his soul to Satan, a court battle ensues, which has some of the show's best satire and pop culture references. Extra points go to the late Phil Hartman, who gives some of his best work as Lionel Hutz in this episode.
01. The Shinning (Treehouse of Horror V, 1994)
Treehouse of Horror V is widely considered the greatest Halloween special the show has ever produced, and the greatest achievement of that episode is undoubtedly The Shinning, the hilarious and pretty terrifying parody of the classic horror film The Shining. It has the family going to a large hotel as the winter caretakers, and when Homer discovers that Mr. Burns, who owns the hotel, cut off the beer supply and cut the TV signal, Homer obviously goes crazy and with the help of ghost bartender Moe and a whole bevy of classic movie monsters, attempts to kill his family. The Simpsons is known for its incredible ability to parody movies, and this is by far their crowning achievement in that regard. It is everything we love about The Simpsons - hilarious, satirical and unbelievably brilliant.
This year's Simpsons' Halloween special, Treehouse of Horror XXV, aired last week on Fox. The episode parodied A Clockwork Orange, The Others and the work of Neil Gaiman.
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