In certain cases the Headless Horseman is considered by some to be a Dullahan. Dullahans are a type of Irish Fae. They usually appear as beautiful women wearing armor and carrying their heads. They ride across the land on an undead horse and are sometimes seen as a sign of an approaching death. If someone sees a Dullahan they are typically drenched in a bucket of blood.
In mythology there is no reference that Dullahans can't cross running water, unlike the Headless Horseman, which is a debating point on the subject. No one knows why that Horseman is unable to cross water if he is in fact a Dullahan. There is also speculation as to why the horseman does not carry his head if he is indeed a Dullahan. Many do argue the point that his head was stolen from him, and that would cause him to hunt out other heads as commonly seen in the story.
It was the Revolutionary War that the Headless Horseman was involved in. His head was taken by a cannon ball, and his body was buried in the Sleepy Hollow Church. According to legend, the Headless Horseman rises every night searching for his head, and if not, he would take someone else's. Ichabod Crane, Sleepy Hollow's school teacher, was first introduced to the legend when Brom Bones told everyone at Baltus Can Tassel's Halloween party about the Horseman. That night, when Ichabod traveled back to Sleepy Hollow, he has a terrifying encounter with the Headless Horseman, resulting in the Horseman throwing his pumpkin head at Ichabod. What happened to Ichabod? Some say he's still alive, while others believe the Headless Horseman took his head. However, Brom Bones was the one behind Ichabod's chase and the legend itself. Ichabod's where-abouts re still unknown.
- In Disney's "Legend of Sleepy Hollow", it is unknown if Ichabod encountered the real Headless Horseman, or if it was just Brom in a costume.
- In the live action film The Hollow, the Horseman wears his pumpkin head through-out the film and has a type of growling sound
- Tim Burton's Sleepy Hollow tells that the Horseman was a Hessian, who did fight in the Revolutionary war, but instead of having his head blown off by a cannon ball, his head was chopped off with his own sword, and was controlled by Katrina's step mother, who stole his head and would blame Baltus for the crime.
- In the 2008 film Scooby-Doo! and the Goblin King, Shaggy and Scooby meet a pumpkin and help him escape a headless horseman.
- In the Television series Sleepy Hollow the Headless Horseman is the first of four, symbolizing an upcoming apocalypse which was prophesied in the book of Revelations, the last book in the Bible. It is said that Ichabod Crane cut off his head similar to the movie by Tim Burton.
- In the Television series The Real Ghostbusters; the Headless Horseman has the appearance as a headless rider riding a motorcycle. After Ichabod Cran escaped him in the past he had since been hunting the descendents of Crane himself around the world. The Ghostbusters soon became involved due to one of the descendents by the name of Kate ran to New York City. It soon came to a final end in which the last remaining descendent of Crane opened the Ghost Trap and trapped the Horseman, ending the family curse forever.
- The Headless Horseman appears in the Scribblenauts games.
- The Headless Horseman's horse appears in the 2014 game Disney INFINITY 2.0..
- The Headless Horsemen appears in Assassins Creed 3 in a Frontier Mission.
- The Headless Horsemen ghost appears walking the paths of skyrim leading you to a skull and a powerful helmet in a graveyard in The Elder Scrolls V: Skyrim.
Manga and Anime
- Celty, in durarara is a dullahan and is looking for her head which was stolen from her