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The Headless Horseman is the main antagonist of Disney's The Legend of Sleepy Hollow (which is based on the 1820 short story of the same name by the late Washington Irving); the second half of Disney's 11th full-length animated feature film The Adventures of Ichabod and Mr. Toad.
The Headless Horseman is voiced by the late Billy Bletcher.
Through the song, Brom Bones tells Ichabod Crane the story of the Headless Horseman, who was beheaded during the Revolutionary War. Every Halloween night he rides in Sleepy Hollow looking for a new head. The best way to escape him is to cross the bridge, as the Horseman's dark powers are limited only to the woods.
That very night, Ichabod rides home alone and keeps imagining that he is being followed as he hears noises while he slowly traverses the forest atop his horse.
When he finds that it is only cattails bumping on a log, Ichabod and his horse hysterically laugh but suddenly stop as another sinister laugh joins them. They both slowly turn around to find the Headless Horseman about to attack them.
He gives chase, laughing all the while. When Ichabod momentarily is trapped on the Horseman's own black steed, he looks down the Horseman's neck to find nothing but evil hollow laughter.
Once you cross that bridge, my friends, the ghost is through, his power ends.
~ Ichabod remembers Bron's song's lyrics to stay safe from the Horseman.
Ichabod runs for the bridge and barely manages to make it across. As Ichabod turns around, he screams as the the black horse rears up and the Headless Horseman throws his head (a Jack o'Lantern set on fire) right at him.
The very next morning Ichabod's hat was found next to a shattered pumpkin, but Ichabod had vanished. Rumors about Ichabod still alive and married to a wealthy widow in a distant county are dismissed, as the good townsfolk of Sleepy Hollow know that he must have been spirited away by the Headless Horseman himself.
House of Mouse
The Headless Horseman regularly appeared in House of Mouse as a recurring guest in the audience, though rarely since he can't speak, thus he's moreso used for one-time gags such as being featured in a Lost & Found commercial where he finds his pumpkin head, being part of Von Drake's song when counting down Disney characters and where they sit, being asked to lend his blade for a moment and, most commonly, scaring Ichabod.
He was naturally allied among the villains during the takeover of the House of Mouse.
The Revenge of the Headless Horseman
The Headless Horseman appeared as the main antagonist in the now-defunct attraction of the same name at Hong Kong Disneyland. When a traveling circus claims that they have found the Horseman's head and are displaying it, the Horseman returns to slaughter and behead them all and reclaim what is his.
The Scariest Story Ever: A Mickey Mouse Halloween Spooktacular
The Headless Horseman makes a cameo in the special The Scariest Story Ever: A Mickey Mouse Halloween Spooktacular where while trick or treating Goofy sees him take the place of a statue and give his iconic laugh much to his horror.
A portrait of the Headless Horseman can be see in the videogame Epic Mickey in Lonesome Manor's library.
It is inexplicably revealed whether or not the Headless Horseman was a real phantom or Brom Bones in disguise (as it was heavily implied in the book that the movie was based on). However, there are some suggestions that the Horseman was indeed an actual phantom, though from what was shown of Ichabod's fearful imagination beforehand, some of these things may have been imagined by him:
Ichabod had looked inside his cloak, revealing nothing to be there.
Brom's horse did not have red eyes and a black mane like the Horseman's did.
Brom needed a saddle, reins, and a bridle to ride his horse, while the Horseman apparently didn't. His implied spiritual nature would likely allow him to remain on his horse without any real support.
The Horseman appeared to be slightly skinnier than Brom.
The Horseman's horse jumped high over a cliff, which no other horse could do.
In many early versions of the Haunted Mansion, the Headless Horseman was to be a focal point of the attraction's graveyard climax.
The Headless Horseman is actually one of the very few Disney Villains to actually "win".
Despite making a small appearance, the Headless Horseman is considered one of the darkest and most disturbing Disney villains.
The Headless Horseman appeared on the Wonderful World of Disney the same Sunday night that The Beatles were on The Ed Sullivan Show.