The tale of Ichabod Crane and the Headless Horseman is almost as iconic as Halloween itself. Another piece of holiday fare from Disney, The Legend of Sleepy Hollow is based on the Washington Irving tale of the same name, which follows the terrifying adventure of Sleepy Hollow's new schoolmaster, Ichabod Crane, battling the town's ghostly Headless Horseman.
Like some of the other Halloween specials on the list, the ending of this tale was anything but happy for Crane - which probably wouldn't sit well with viewers wanting to see Halloweentown II: Kalabar's Revenge, even with Bing Crosby narrating it. The Legend of Sleep Hollow was originally the second-half of The Tale of Ichabod Crand and Mr. Toad.
Where to watch it now: YouTube