The spooky season of Halloween is upon us once again and if you’re anything like me, you’re no doubt indulging in your favorite Halloween traditions. Carving jack-o-lanterns, making costumes, eating ungodly amounts of candy, and of course, watching a scary movie. But one tradition that I love that I feel is often unfairly neglected would have to be the annual viewing of specific Halloween TV specials.
While not as prominent in the cultural zeitgeist as Christmas specials, Halloween specials provide the ghoulish frights, autumnal atmosphere, and all-around fun of All Hallow’s Eve in bite-sized packages while allowing us to view some of our favorite characters in an entirely new light. And that is especially apparent in the medium of animation.
Before we begin, I just want to say that there are a lot of great animated Halloween specials out there and I most definitely left out some excellent candidates if only for the sake of narrowing things down Also, to ensure both fairness and variety, this list contains only one entry per franchise. So, without further a do, here are my picks for the Top 5 BEST animated Halloween specials.
Also Read: The 7 Best Halloween Games To Play Before The End of October
#5. A Pinky and The Brain Halloween
On Halloween night, after yet another of Brain’s world domination plans goes wrong, a mysterious and seemingly all-powerful being named Mr. Itch, a clear stand-in for Satan himself, gives Brain a Faustian bargain: the world in exchange for his soul. Brain refuses, but Pinky, in an effort to make his best friend happy, takes the deal instead.
Despite finally getting everything he ever wanted, Brain finds himself unsatisfied with ruling the world without his best friend by his side and journeys into the depths of Hell to rescue Pinky from eternal torture. Although Brain technically loses his battle against Mr. Itch, a loophole in the original contract ultimately sets Pinky free; with the two escaping from Hell and living to take over the world another day.
The trademark intellectual wit amidst increasingly ridiculous situations that defines Pinky and The Brain is very much on display here. Tons of clever and hysterical dialogue mixed in with some great visual gags and a surprising amount of heart for what it is. And it even manages to make Mr. Itch a legitimately threatening presence when he needs to be. The perfect balance of humor, scares, and heartfelt emotion for the spookiest time of the year.
#4. “Summerween” from Gravity Falls
Almost any episode of the wonderland of weirdness that is Alex Hirsch’s Gravity Falls could potentially work as a Halloween episode, but this is the only one that actually takes place on Halloween…… kind of. In a clever work-around to do a Halloween special despite the show taking place entirely in Summer, the writers decided that everyone in the town of Gravity Falls loves Halloween so much that they celebrate it twice a year: once in the usual time of October and once in June.
Twins Dipper and Mabel are immediately enamored by the Summerween concept and begin prep for trick-or-treating when Dipper’s unrequited crush Wendy invites him to a “cool teens” Summerween party. And the horrifying beast known only as The Summerween Trickster is no fan of Dipper’s lack of holiday spirit as he attempts to ditch trick-or-treating; challenging the twins and their friends to collect five-hundred pieces of candy by the end of the night or lose their lives.
The No-Face inspired horror of The Summerween Trickster, the race against the clock to get as much candy as possible, and the emotional struggles that both Dipper and Mabel have regarding their relationships to Halloween as they get older are all very compelling and surprisingly well-balanced; even when you add in the subplot about Grunkle Stan trying to scare trick-or-treaters. And the final twist with the Trickster’s true origin is too brilliant for me to spoil here if you’ve somehow never seen one of the best episodes of one of the best cartoons ever made for yourself.
#3. “Thanks To Them” from The Owl House
Like with Gravity Falls, almost any episode of the macabre yet wholesome masterpiece of urban fantasy storytelling that is Dana Terrace’s The Owl House could potentially work as a Halloween story. But not only is this the only one to actually take place on Halloween, at least in part, it’s also one of the rare holiday episodes of a show that incorporates the holiday in question into the show’s ongoing plot and character arcs.
See, “Thanks To Them” serves as the first of three hour-long specials that make up the show’s third and final season, picking up directly after Season 2’s epic cliffhanger; wherein neurodivergent outsider teen turned witch-in-training Luz Noceda ended up back in the human realm alongside several of her compatriots from her time in the Boiling Isles. Specifically, her girlfriend Amity, her two best friends Willow and Gus, and enemy turned ally Hunter, who are now all separated from their families as the all-powerful imp The Collector rains down chaos on the Demon Realm.
As Luz and Hunter struggle with their roles in the villain plot, specifically how Luz accidentally helped main antagonist Emperor Belos meet The Collector, and Luz’s friends attempt to solve an ancient rebus that will hopefully guide them to a portal back to the Demon Realm; Luz’s hometown of Gravesfield is preparing for its annual Halloween Festival, which in turn helps tie the holiday directly into the episode’s main theme: the positives and negatives of being someone you’re not, or at least pretending to be.
The whole idea of Halloween costumes is all about adapting a new identity and that concept is seen throughout “Thanks To Them” in both positive and negative ways. Shapeshifter Vee taking on her own form instead of just looking like Luz, Hunter finding comfort in a Star Trek pastiche called “Cosmic Frontier,” Belos possessing Hunter in the climax, Luz trying and failing to just be normal when that just isn’t her, and of course the gang’s Halloween costumes that end up being their main outfits for the rest of the season. Genuine scares, authentic atmosphere, and the excellent character work and story The Owl House is known for make this a perfect Halloween watch.
#2. It’s The Great Pumpkin, Charlie Brown
In my opinion, a holiday isn’t a true holiday unless there’s a Peanuts special about it. Charles Schulz’s beloved creations never fail to bring a smile to my face and are a quintessential component of nearly every holiday tradition cycle; with Halloween being no exception and Great Pumpkin being one of my personal favorite entries in the larger Peanuts canon.
While Charlie Brown and the other members of the Peanuts gang go out for trick-or-treating and later to the annual Halloween party, Linus spends the night in a pumpkin patch waiting for The Great Pumpkin, a mythical creature that gives out presents to the most sincere children in the world every Halloween. At least according to Linus. He manages to convince Sally to stay in the pumpkin patch with him and when The Great Pumpkin fails to show up; Sally lets loose on him in a legendarily hilarious fit of rage.
That’s an often overlooked element of most of Peanuts that especially comes up here. Even after over fifty years and even amidst the broader cultural view of the franchise as strictly defined by wholesomeness and innocence, It’s The Great Pumpkin, Charlie Brown is still incredibly funny. Linus crying over Lucy “killing” the pumpkin, one of the best variations on the football gag, Charlie Brown’s head being used as a jack-o-lantern model, Snoopy’s Flying Ace subplot, “I got a rock,” it’s all genuinely hilarious and it all serves to make Great Pumpkin essential viewing every Halloween.
#1. The Simpsons’ Treehouse of Horror V
The Simpsons‘ annual Treehouse of Horror episodes not only make up some of the best Halloween specials, but arguably some of the best episodes of television ever made. The anthology format, spot-on parody, and often surprisingly intense scares make them perfect viewing for Halloween and to be honest, if I didn’t have a one entry per franchise rule, this entire list would likely just be Treehouse of Horror episodes.
But for me, the fifth installment of the beloved subseries remains the best, namely because it’s one of the only Treehouse of Horror episodes where all three segments are equally great. First up is “The Shinning” a spot-on parody of The Shining with Homer taking the Jack Torrance role as he’s driven insane by a lack of beer and cable TV. Next, “Time and Punishment” sees Homer travel to multiple apocalyptic alternate futures after accidentally inventing time travel while trying to repair the toaster. Finally, “Nightmare Cafeteria” shifts the perspective to Bart and Lisa as Springfield Elementary’s lunch menu gets a cannibalistic update.
All three segments are perfectly paced, filled with countless memorable quotes, and even manage to create a genuinely foreboding atmosphere and some legit scares. Homer nearly killing Marge in “The Shinning,” the lobotomized Simpson family in “Time and Punishment,” and especially the escalating sense of dread in “Nightmare Cafeteria” add a layer of genuine horror that turn what is already a brilliant comedy into something truly special. It’s what makes Treehouse of Horror V the best Treehouse of Horror installment and in turn the best animated Halloween special.
Follow us on Facebook, Twitter, Instagram, and YouTube for more entertainment coverage.
