The Headless Horseman is a beheaded undead man later resurrected in the 21st Century Sleepy Hollow with Crane, where he was revealed to be the First of the Four Horsemen of the Apocalypse: Death.

He was Crane's best friend until he found out that Katrina broke her betrothal with him because she was in love with Crane, after which he became the horseman so he could get revenge. He later holds her captive, but she escapes back to Crane. He believes that he was meant to be the hero of his story, but that Crane was the one who turned him into a villain. After Abbie and Crane save him from being destroyed by a fallen angel, he reluctantly agrees to leave them alone and abstain from killing in exchange for Katrina being allowed to attempt to return him to his mortal form.