First off, we’ve disqualified The Nightmare Before Christmas and Hocus Pocus. Firstly, because they’re not obscure, and secondly because they’d win. No contest.
The Worst Witch (1986)
Before there was Harry Potter, there was Mildred Hubble, a fairly incompetent-yet-talented witch at Miss Cackle’s Academy for Witches. She learns from the dotty, lemon-drop-fancying Dumbledore Miss Cackle, is somewhat harassed by the strict, black-wearing teacher with a grudge, Severus Snape Miss Hardbroom, and gets bullied by a snobby rival who believes in blood purity, Draco Malfoy Ethel Hallow. But luckily Mildred has the help of her two best friends in the world, Ron Weasley and Hermione Granger Maud Spellbody and Enid Nightshade.
The book series, which first came out in 1974, has had several adaptations. The one from 1986 features a green-screen-loving Tim Curry, showcases Fairuza Balk before The Craft, and is absolutely bananas. Unfortunately, it’s fairly hard to get your hands on.
There is also a newer adaptation. It happens to have the little Mormont lady from Game of Thrones.
But remember, kids – anything could happen on Halloween. Your teacher could turn into a sardine. Your dentist could turn into a queen. HAS ANYBODY SEEN MY TAMBOURINE?!
A considerably later, 90s-style classic with possibly the most charismatic grandmother you’ve ever seen in your life, Halloweentown is the source of magic, bad effects, and a great deal of over-acting from child stars.
Aggie Cromwell is played by Hollywood royalty Debbie Reynolds – yes, that Debbie Reynolds. After Carrie Fisher’s and Debbie Reynolds’s death only a day apart in 2016, many people were re-watching their favorite films from their huge filmography. Star Wars, for Carrie Fisher and Singin’ in the Rain, for Debbie Reynolds were most often cited. Halloweentown got somewhat ignored, but this piece of cheesy made-for-TV goodness is definitely worth a re-watch.
(We could also talk about the other stars, the spooky-wooky town and the typical YA plot, but honestly Reynolds steals the show.)
Halloween is Grinch Night (1977)
Let’s be real: Grinch Night is an acid trip. We don’t know what our parents were thinking for letting us watch it.
Sure, it starts pretty chill: The people of Whoville decide to hide when they smelled the sour-sweet wind coming over the hill. (They don’t want to go out when the Grinch out, though $6.60 seems like a very specific amount.) But then the prequel to How the Grinch Stole Christmas! goes a bit off the rails when Euchariah takes a hit of some manner of illegal substance jumps into the Grinch’s wagon. Hope you enjoyed nightmares as a four-year-old.
But we love Halloween. It’s a wonderful night for eyebrows.
Raggedy Ann and Andy in The Pumpkin Who Couldn’t Smile (1979)
An extremely depressed pumpkin that cries tears of pumpkin seeds is both adorable and tragic. It stars Raggedy Ann and Andy, who had their own musical adventure of chaos and nightmares. (Fun Fact: those who saw that 1977 film as children grew up into adults who now question whether the supposedly benevolent force behind our universe is actually a terrifying demigod forcing us into horrors for its own entertainment.)
This nostalgic Halloween special is relatively harmless though. Raggedy Ann and her male alternate self brings a sad little boy and a sad little pumpkin together, and makes the evil aunt Agatha considerably less sad.
The Adventures of Ichabod and Mr. Toad (1949)
This film was one of several collections of shorts Walt Disney used to get the company back on its feet in the post-WWII era. It includes several stories, but one left a significantly larger impression on the audience, namely the one created after Washington Irving’s ghost story. Narrated by Bing Crosby, this show has been airing around Halloween on American televisions since the 50s.
It’s the Great Pumpkin, Charlie Brown (1966)
No one can smash together religious metaphors and squash varieties quite like Charles M. Schulz. The original comic strip was actually satire; Shultz found the concept of believing in Santa Claus sacrilegious and ridiculous. That being said, this special is almost as beloved as the very quotable Christmas special.
Linus’s cult may have failed, but the cult around this movie seems to get bigger every year.
Mad Monster Party? (1967)
Speaking of cults, this lesser-known Rankin/Bass production has a very small cult following. Who’s to blame them? Not many parodies actually feature Boris Karloff. Baron Boris von Frankenstein wants to retire from the monster-making business, but has a bit of trouble electing a successor.
The Halloween that Almost Wasn’t (1979)
Dracula (played by Judd Hirsch) and his cast of spooky friends (including the Wolfman, the Mummy, Igor, and Frankenstein’s Monster) are concerned that no one takes Halloween seriously anymore because monsters are now funny, not scary. There’s an evil witch who’s sick of being called ugly, and a celebratory disco scene at the end. It’s very 70s.
Disney’s Halloween Treat (1982)
A mishmosh of clips from various animated Disney features and a handful of classic shorts created this special, narrated by a jack-o’-lantern. There have been several Disney Halloween specials over the years, usually cutting between segments using a famous narrator. These segments usually feature the demon from Fantasia as well as a sampling of clips of past villains, such as Mad Madam Mim.
Garfield’s Halloween Adventure (1985)
Somebody told Garfield he could get a whole bunch of free food. Of course shenanigans ensue. (Pirates and ghosts make their way in there too.)
Mr. Boogedy (1986)
A salesman and his family move to a house that’s already full of ghosts from the colonial period. What’s that, you say? It’s uncomfortably similar to The Haunted Mansion? Let’s not talk about The Haunted Mansion, shall we?
Did we forget your favorite? Let us know in the comments below!