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With a hip-hip and a clippity-clop He's out looking for a top to chop So, don't stop to figure out a plan You can't reason with a headless man!
„
~ Song lyrics about the Headless Horseman
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 an unknown voice actor.
The story of the Headless Horseman may as well be the same as the original tale; a Hessian soldier during the American Revolution whose head was blown off by a cannonball. Legend has it that after his death, he became a malevolent specter who rides through the woods near Sleepy Hollow in search of a new head to replace his original one.
At some point afterwards, a new resident named Ichabod Crane comes to Sleepy Hollow and eventually competes with Brom Bones for the affection of local heiress, Katrina Van Tassel. During a Halloween party at the Van Tassel house, Brom learns of Ichabod's fear of superstitions and decides to use it to his advantage. He tells the other guests of how ghosts and demons get together in the forest every Halloween night, including the Headless Horseman, which scares Ichabod out of his wits. Brom also claims that he encountered the Horseman himself one year prior, but was able to escape by crossing the wooden bridge spanning over the brook, since the Horseman's powers were limited to the woods.
The Chase[]
The Horseman chasing after Ichabod.
That very night, Ichabod rode atop his horse, Gunpowder home alone through the woods that Horseman appears in. During the trek, he saw several trees shaped like ghouls and heard animal noises seemingly calling his name, and became deathly afraid that these were the spooks that Brom spoke of. Upon ending up in a graveyard, Ichabod began to hear galloping hooves that weren't coming from Gunpowder, since he had fallen asleep. Believing that the Headless Horseman was coming for him, he desperately tried to rouse his horse up for a quick retreat, only to end up falling backwards on top of a log that some cattails were bumping onto, which was what he was hearing. Realizing that it was all just his imagination, a relieved Ichabod began to hysterically laugh along with Gunpowder, until another sinister cackle suddenly joined them. They both then slowly turned around and saw the Headless Horseman riding on a black, red-eyed horse and holding a gleaming sword and a flaming, skull-shaped jack-o-lantern.
Deathly frightened, Ichabod and Gunpowder began their escape and the Horseman gave chase, laughing all the while. Upon getting close enough that Ichabod could feel the black horse's breath on his neck, the Horseman immediately attempts to decapitate Ichabod with his sword. Ichabod survives and both he and Gunpowder go down a hill, with the Horseman jumping over them. Ichabod fails to notice this and assumes that the ghost was gone when he couldn't see him, only for the Horseman to make another attempt as soon as Ichabod got close enough again. Ichabod and his horse fall down another hill into a river and then attempt to escape the woods to the bridge, but the Horseman appears to block their exit while swinging his sword, though Ichabod escapes yet again.
Using a tree, Ichabod swings both himself and Gunpowder away from the Horseman's pursuit and back towards the bridge. At that point, Ichabod remembers what Brom said about the Horseman's weakness and brims with confidence in his survival. However, while slipping on the mud on the road to the bridge, Gunpowder ends up going into the opposite direction, towards the incoming Horseman. When both horses and their riders collide, Ichabod, he looked down the Horseman's neck and became utterly terrified by what he saw, with the Horseman laughing in evil amusement.
The Horseman then attempts to behead both Ichabod and Gunpowder, but they retreat and both riders and their horses begin circling around a tree. During this, Ichabod ends up hitting his neck on a tree branch and swings from his horse to the other one right behind the Horseman. Once again, Ichabod fails to notice what happened until he saw Gunpowder behind him, gulping in terror. He then hits the same branch as before and swings back onto his own horse.
The Horseman throwing his pumpkin head at Ichabod and possibly killing him.
Once that was over, Ichabod and Gunpowder make their way to the bridge with the Headless Horseman closing in from behind. They then finally make it to the bridge's entrance, where the Horseman is forced to stop. After crossing the bridge Ichabod stops and looks behind, believing himself to be safe, but then his comfort quickly turns to sheer panic as the Horseman throws a flaming jack-o-lantern straight at Ichabod.
Aftermath[]
The very next morning, Ichabod's hat was found next to a pair of hoof-prints and a shattered pumpkin, and that Ichabod himself had completely vanished along with his horse. With Crane gone, Brom was able to marry Katrina without competition. Rumors then circulated about Ichabod still being alive and married to a wealthy widow in a distant county, but they were dismissed, as the good townsfolk of Sleepy Hollow firmly believed that he must have been spirited away by the Headless Horseman.
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.
Quotes[]
“
Yaaaah-ha-ha-ha-ha-haaaa!
„
~ The Headless Horseman's evil laugh.
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.
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.
