The Headless Horseman

The Headless Horseman is the main antagonist from Disney's 1949 short The Legend of Sleepy Hollow, segment of the hit The Adventures of Ichabod and Mr. Toad. He also appears at any Disney Parks for Halloween events including the not so scary Halloween party.

The Legend of Sleepy Hollow
IBrom 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 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 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 in the House of Mouse as one of the guests.

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.

Trivia

 * It is unknown whether or not the Headless Horseman was a real phantom or Brom Bones in disguise (as it was in the book that the movie was based on).