The Headless Horseman

The Headless Horseman is the main antagonist from The Legend of Sleepy Hollow, the second half of The Adventures of Ichabod and Mr. Toad.

The Legend of Sleepy Hollow
Brom Bones tells Ichabod Crane the story of the Headless Horseman, who lost his head long ago 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. When he finds that it's only cattails bumping on a log, Ichabod and his horse hysterically laugh but suddenly stop as another 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. Ichabod runs for the bridge and barely manages to make it across. As Ichabod turns around, he screams as the black horse rears up and the Headless Horseman throws a flaming jack o' lantern right at him. The very next morning, Ichabod's hat was found next to a shattered pumpkin. However, Ichabod had vanished. Rumors about Ichabod still alive and married to a wealthy widow in a distant county are all but 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 appears House of Mouse, as a recurring guest in the audience.

Disney Parks
The Headless Horseman is part of various Halloween festivities at Walt Disney World, leading the Boo to You Parade at Mickey's Not So Scary Halloween Party and being the center of a Sleepy Hollow themed haunted hayride at Fort Wilderness.

At Hong Kong Disneyland, the Headless Horseman is set to be the host of the 2011 Halloween festivities. He will lead the Halloween parade and star in a new haunted maze in Adventureland. Here, a member of an Adventurers Club has claimed to have found his head and is presenting it in a sideshow exhibit, provoking the Horseman's wrath.

The Horseman also has a spell card known as "The Headless Horseman's Exploding Jack-O-Lantern" in the attraction Sorcerers of the Magic Kingdom.

Trivia

 * It is unknown 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, Ichabod had looked inside his cloak, revealing nothing to be there, suggesting that the Horseman was indeed an actual phantom. Additionally, Brom's horse did not have red eyes like the Horseman's did.
 * It is unknown how the Horseman was able to ride his horse without falling off, since he didn't have a saddle or reins or a bridle of any kind. However, the Horseman's implied spiritual nature would likely allow him to remain on the horse without any real support.
 * A portrait of the Headless horseman can be see in the video game Epic Mickey; in Lonesome Manor's library.
 * The Headless Horseman is actually one of the very few Disney Villains to actually "win" rather than being defeated at the end of his/her film.
 * Despite making a small appearance, the Headless Horseman is arguably considered the darkest and most disturbing Disney villain.
 * It can be argued if the ghost was real or not. Brom Bones was likely the ghost in disguise as the ghost had a similar body build to Brom Bone's and rode on a horse that resembled Brom Bone's horse, as well as the sword and pumpkin looking like the ones seen at the van Tassel party. However there is also proof the ghost may have been real as Ichabod peered into the ghost's headless neck and saw nothing but evil laughter as well as the fact it would have to be impossible for Brom to see Ichabod from under his top. Brom himself even claimed he saw the ghost. But it is possible, though unlikely, that the ghost was really just Ichabod's imagination.