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The Headless Horseman is a villain who appeared in the television special Wicked Woods: A Descendants Halloween Story, and 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.


Before the formation of Auradon[]

      Further information: The Adventures of Ichabod and Mr. Toad


The Headless Horseman as he appears originally in The Legend of Sleepy Hollow.

He appears when Ichabod was riding home alone and was imagining that he is being followed. When Ichabod finds that it's only cattails bumping on a log, he and his horse hysterically laugh, but suddenly stop as another, more sinister 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. 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.

Wicked Woods: A Descendants Halloween Story[]

Audrey and Uma disguised themselves as the horseman to scare Mal, Evie, Jay, and Carlos. However, soon they encounter the real Headless Horseman. Mal gives him some old-fashioned butterscotch candy which turns out to be his favorite. And the horseman rides way, wishing them a happy Halloween.


  • Despite making a small appearance in his debut film, the Headless Horseman is considered one of the darkest and most disturbing Disney villains.
  • He is one of the very few Disney villains to actually "win" rather than being defeated at the end of his/her film.
  • He is the only villain to never be imprisoned on the Isle of the Lost, living hidden in the forests of Auradon.
  • He is one of the few villains without a known descendant. In his case, he likely does not have a child, by living hidden from the rest of the world.