The Legend of Sleepy Hollow
First airing in 1949, this Bing Crosby-narrated Disney version of Washington Irving’s classic tale is one of the best adaptations of Ichabod Crane and the Headless Horseman you can find, with its combination of New England cozy and Halloween spooky. It isn’t currently available on DVD, but you can watch it on YouTube.
The Skeleton Dance
This classic 1929 Disney classic was adapted from Camille Saint-Saëns’ composition Danse Macabre, and features skeletons dancing the Charleston.
The Cobweb Hotel
This 1936 cartoon, featuring a talking spider that sounds like a grandmother from the old country getting over laryngitis, came from one of Disney’s biggest competitors, Fleischer Studios.
Trick or Treat
Why does Donald Duck always feel the need to mess with his nephews? In this 1952 Halloween cartoon, Witch Hazel gets involved in all the Duck family zaniness, and it doesn’t take long for things to get hilarious.
Chuck Jones admitted that he got the idea for his idea for a Looney Tunes Witch Hazel from the Disney character, but since she goes up against Bugs Bunny, we won’t give her a hard time.
Our old pal Mickey Mouse just wants to get away from the storm, but he ends up having to entertain a bunch of skeletons and other undead creatures in this 1929 short.
Betty Boop’s Hallowe’en Party
Because there ain’t no party like a 1933 Betty Boop party with a bunch of dancing forest creatures.
Bugs tries to get to Pittsburgh, but takes a wrong turn and ends up dueling with a vampire in this 1963 short.
There’s Good Boos Tonight
Casper is sort of a boring ghost, but this 1948 cartoon is endearing enough.
The Headless Horseman
And to round it out, we present this 1934 ComiColor cartoon version of the Headless Horseman tale.