The Headless Horseman is a Heartless Commander in the Villain League, and is the Big Bad from 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 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.
Role in the series
The Headless Horseman has been summoned by Maleficent to provide the Villain League with a villain commander to the Heartless. as of matter of fact, the Headless horsemen did appear, but not as what is writen, he was one of the briefly appearing summoned monsters of cobra to aide the wyvern twins and the Transilvainian monsters in Spongebob and Friends find the black cauldron. the horsemen has not made much appearences after that.