Brom Bones tells Ichabod Crane the story of the Headless Horseman, who is the worst ghost in all of Sleepy Hollow. Every Halloween night he rides in across the countryside, looking for his head. If he can't find it, he'll take other people's heads to replace it. The only way to escape him is to cross the bridge near the church, as the Horseman's dark powers are limited only to the woods.
That very night, Ichabod rides home alone on his horse Gunpowder and keeps imagining that he is being followed. When he finds that it's only cattails bumping on a log, Ichabod laughs hysterically before being joined casually by Gunpowder. But both rider and horse 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. 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. Ichabod tries to dodge the horrible missile, but too late. He gets struck in the head and tumbles off Gunpowder into the dust.
The very next morning, Ichabod's hat is found next to a shattered pumpkin. However, Ichabod has vanished since Brom and Katrina Van Tassel are married. 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 (or most likely killed) by the Headless Horseman himself.
The Headless Horseman makes a very brief cameo in the Darkwing Duck episode "Monsters R Us", in which he appears from behind a closed door inside the home of Morgana Macawber. When Darkwing pays Morgana a surprise visit and finds find her house to be empty, he looks around for her before opening one of her doors to reveal the Horseman surrounded by a fire. Angered, the Horseman rides forward and tramples over Darkwing in his path, leaving horseshoe marks all over the poor hero's body.
The Headless Horseman appears in House of Mouse, as a recurring guest in the audience. In "Where's Minnie?", the Headless Horseman is featured in a commercial for Scuttle's Lost & Found, the lost and found service provider for the House of Mouse nightclub.
In "Rent Day", the Horseman is one of many guests Mickey Mouse attempts to make a trade with in order for Mickey to get the fifty dollars he needs to pay the rent for the nightclub. When bargaining with the Horseman, Mickey offers to get him a pumpkin as a new head if the Horseman would give his sword to Mickey. Ultimately, however, Mickey is unable to fulfill any of his trades, so the Horseman got to keep his sword.
When Pete takes over the nightclub in "Pete's House of Villains", the Horseman takes over Clarabelle Cow's duty of hosting the Main Street Gossip segment, which leaves many of the guests unsatisfied since the Horseman lacks a head with which to speak any gossip at all.
The Headless Horseman is briefly mentioned by the King, who says he once displeased him, and subsequently "lost his head", implying that the Horseman was beheaded on order of the King.
The Headless Horseman makes a cameo in the special "The Scariest Story Ever: A Mickey Mouse Halloween Spooktacular", where while trick-or-treating, Goofy sees him take the place of a statue and give his iconic laugh, much to his horror.
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.
At Hong Kong Disneyland, the Headless Horseman was the host of the 2011 Halloween festivities. He leads the Halloween parade and starred in a new haunted maze in Adventureland, The Revenge of the Headless Horseman. Here, a member of an Adventurers Club has claimed to have found his head and is presenting it in a sideshow exhibit, provoking the Horseman's wrath. This attraction proved popular enough to become a recurring feature of the event.
The Headless Horseman made his debut as part of Mickey's Halloween Party at Disneyland in 2016, leading the Frightfully Fun Parade. A statue of the Horseman has also become a central feature of Disney California Adventure's Halloween festivities on Buena Vista Street.
In World of Color: Villainous!, the Headless Horseman is the last villain to appear in the villain montage (as well as the last one to be introduced in the Halloween special). As the Queen of Hearts shouts "Off with their heads!", the Horseman appears laughing maniacally wielding his sword and pumpkin head, which he throws at the audience causing a fiery explosion with actual flame streams rising up.
The Horseman also has a spell card known as "The Headless Horseman's Exploding Jack-O-Lantern" in the attraction Sorcerers of the Magic Kingdom.
- It is unknown whether or not the Headless Horseman was a real phantom or Brom Bones in disguise (as it was heavily implied in the book on which the movie was based). However, there are some suggestions that the Horseman was indeed an actual phantom, for even when Ichabod's fearful imagination is shown beforehand, Gunpowder could not have imagined it all after hearing that frightful laugh. Some of these things appear to confirm the existence of the Horseman:
- Ichabod had looked inside his cloak, seeing nothing there.
- However, he might have screamed because he didn't expect to see Brom, rather than not expecting to see nothingness, and he finally acknowledged that Brom was a severe threat to his life. This is supported by the Horseman slashing even harder once Ichabod looked inside.
- Brom's horse did not have red eyes and a black mane like the Horseman's did.
- Brom needed a saddle, reins, and a bridle to ride his horse, while the Horseman apparently didn't. His implied spiritual nature would likely allow him to remain on his horse without any real support.
- Additionally, the Horseman's horse jumped high over a cliff, and was ahead of Ichabod briefly. No horse, let alone Brom's, could jump that high, and the Horseman remained in his saddle too.
- The Horseman appeared to be slightly skinnier than Brom.
- The Horseman pulled his fiery pumpkin head out of nowhere when he threw it at Ichabod, almost as though it were by magic.
- Ichabod had looked inside his cloak, seeing nothing there.
- It is unknown how the Horseman died as it was never stated in the film. In the original short story, it is said that he was a Hessian soldier whose head was blown off by a cannonball during the Revolutionary War.
- According to a tour of the Old Dutch Church's cemetery at Sleepy Hollow, the body of the Hessian was buried in an otherwise normal patch of grass, due to him saving the life of the infant daughter of a wealthy family, despite both being on opposite sides of the American Revolution. The name of the family was "Van Tassel".
- In many early versions of the Haunted Mansion, the Headless Horseman was to be a focal point of the attraction's graveyard climax.
- The Headless Horseman is one of the very few Disney villains to actually "win" rather than being defeated at the end of his/her film.
- A portrait of the Headless Horseman can be seen in the video game Epic Mickey; in Lonesome Manor's library.
- Despite making a small appearance, the Headless Horseman is considered one of the darkest and most disturbing Disney villains. He is also considered one of the scariest villains in any Disney canon and Disney still receives complaints from parents about him frightening children.
- The Headless Horseman appeared on The Wonderful World of Disney the same Sunday night that the Beatles made their first appearance on national TV on The Ed Sullivan Show.
- The maniacal laugh of the Headless Horseman has become a common stock sound effect in Halloween-themed cartoons as "EvilManLaughsWrev CRT024102", as catalogued by Sound Ideas. It is a modified version of "EvilManLaughs3x CRT024101" with added reverberation.
- The Headless Horseman makes a cameo in the Broken Karaoke video, 'Where Are All the Monsters'.