The Headless Horseman is the main antagonist of The Legend of Sleepy Hollow, the second half of Disney's 1949 animated feature film 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, sword at the ready. 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 (most likely killed) by the Headless Horseman himself.