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The Headless Horseman is the main antagonist of Disney's The Legend of Sleepy Hollow (which was 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's iconic and sinister laugh was provided by the late Billy Bletcher.
Through the song, Brom Bones told Ichabod Crane the story of the Headless Horseman, who was the ghost of a Hessian soldier whose head was blown off by a cannonball during the Revolutionary War. Every Halloween night, the Headless Horseman rides in Sleepy Hollow looking for a new head. With the only way to escape him being to cross the bridge, as the Horseman's dark powers were limited only to the woods.
That very night, Ichabod rode home alone and kept imagining that he was being followed as he heard noises of galloping hooves while he slowly traversed the forest atop his horse.
The Horseman chasing after Ichabod.
After he found that it was only cattails bumping on a log, Ichabod and his horse, Gunpowder, hysterically laughed but suddenly stopped as another sinister laugh joined them. They both then slowly turned around and found the Headless Horseman about to attack them.
He then gave chase, laughing all the while. When Ichabod was momentarily trapped on the Horseman's own black steed, he looked down the Horseman's neck and found 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.
The Horseman throwing his pumpkin head at Ichabod and possibly killing him.
Ichabod then ran for the bridge and barely managed to make it across. As Ichabod turned around, he screamed as the black horse reared up and the Headless Horseman threw his head (a flaming jack-o-lantern) right at him.
The very next morning, Ichabod's hat was found next to a shattered pumpkin, but Ichabod had vanished. Rumors then circulated about Ichabod still being alive and married to a wealthy widow in a distant county were dismissed, as the good townsfolk of Sleepy Hollow knew that he must have been spirited away by the Headless Horseman himself.
Other Media[]
House of Mouse[]
The Horseman being talked to by Mickey Mouse in House of Mouse.
The Headless Horseman regularly appeared in House of Mouse as a recurring guest in the audience, though rarely since he couldn't speak, thus he's more so used for one-time gags such as being featured in a Lost & Found Commercial where he found his pumpkin head, him being asked to host a gossip table and failing to do so due to missing his head, being part of Von Drake's Song when counting down Disney Characters and where they sat, 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 in House of Villains.
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 claimed that they had found the Horseman's Head and were displaying it, the Horseman returned to slaughter and behead them all and reclaim what was his, however much of the attraction's layout is unknown.
The Scariest Story Ever: A Mickey Mouse Halloween Spooktacular[]
The Headless Horseman made a cameo in the special The Scariest Story Ever: A Mickey Mouse Halloween Spooktacular where while trick or treating, Goofy saw him take the place of a statue and give his iconic laugh much to his horror.
Epic Mickey[]
A portrait of the Headless Horseman could be see in the video game, Epic Mickey in Lonesome Manor's Library.
Darkwing Duck[]
The Horseman makes a cameo in the episode "Monsters R Us", where runs over Darkwing flat after he opens a door in a haunted house.
Trivia[]
Ichabod looking down the Horseman's cloak.
It was never 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 were some suggestions that the Horseman was indeed an actual phantom due to the evidence below.
Ichabod looked inside his cloak, only to be terrified of what he saw implying nothing, bones, or a bloody stub.
Brom's Horse did not have red eyes like the Horseman's did.
The Horseman appeared to be slightly skinnier than Brom.
The Horseman came close to beheading Ichabod several times during the chase. While Brom was a bully and may have wanted to scare Ichabod out of town, it's doubtful that he would have actually tried to kill Ichabod.
A likely explanation for all of these is that we are seeing the chase through Ichabod's eyes, as two of the segments animators, Frank Thomas and Ollie Johnston, said that a lot of the forest scene was embellished by Ichabod's fears, likely meaning the Horseman chase was as well, this could explain the close calls the Horseman had to killing Crane, simply being exaggerated in Crane's mind, and what Ichabod thinks he sees or doesn't see down the Horseman's throat.
In many early versions of the Haunted Mansion, the Headless Horseman was to first appear in a "window" of the manor in a flash of lightning, riding toward the mansion, and the focal point of the attraction's graveyard climax.
The Headless Horseman was actually one of the very few Disney Villains to actually "win".
Despite making a small appearance, the Headless Horseman was considered one of the darkest and most disturbing Disney villains and a fan favorite.
The Headless Horseman appeared on the Wonderful World of Disney the same Sunday night that The Beatles were on The Ed Sullivan Show.
The Horseman's song is one of the few Disney villain songs that is not directly sung by the villain themselves.
It is unknown if the Horseman was ever able to kill someone yet making Ichabod his first victim, or that his previous head's have rotted away.
There is an inconsistency with the Horseman's head as a few shots such as his introduction depict his head as a burning, black skull, while other shots depict it as a flaming jack-o-lantern.
