A painting by John Quidor of the headless horseman chasing Ichabod Crane
painting by John Quidor (1858)

The Faces of Sleepy Hollow

The legend of Headless Horseman has taken many forms in film over the course of cinema history. He is traditionally depicted as a man on horseback who is missing his head and is searching for it. The most famous myths come from the short story of “The Legend of Sleepy Hollow,” written in 1820 by Washington Irving.

The first film adaptation was The Headless Horseman in 1922. The film was the first panchromatic black-and-white feature film, meaning a type of black-and-white photographic emulsion that is sensitive to all wavelengths of visible light, making the film look more realistic. The plot follows the village of Sleepy Hollow, which is getting ready to greet the new schoolteacher, Ichabod Crane, from New York. Crane has already heard of the village’s legendary ghost, a headless horseman who is said to be searching for the head that he lost in a great battle. Arriving in town, the schoolteacher quickly begins to pursue the beautiful young heiress, Katrina Van Tassel. This angers Abraham Van Brunt, who is courting her. Once Ichabod Crane becomes pursued by the Headless Horseman, it can be assumed that Brunt is behind it.


An image from Disney's The Adventures of Ichabod of the headless horseman attacking Ichabod CraneDisney’s 1949 animated film The Adventures of Ichabod, follows a very similar plot with its cheery musical tempo. The biggest difference is that Ichabod confirms, during his chase, that the Headless Horseman is indeed real. Although the film ends with the possibility of Ichabod’s death, Disney does a good job of ending on a lighthearted note.

There are several other renditions of Headless Horseman films throughout the years, but the most well known one has to be Tim Burton’s Sleepy Hollow. The interesting thing about this film, other than capturing the essence of Burton’s mind, is that the film seems to play more as a true story that could have inspired the other films as legends or myths told by campfire. Now take that with a grain of salt as there is witches and black magic in this film. Not that I’m saying witches aren’t real…

Ichabod Crane, played by Johnny Depp, is a New York detective and not a teacher this time. He is sent to Sleepy Hollow to investigate the murders in the town and prove to his superiors that science can be effectively used to solve crimes. What he discovers is that the Headless Horseman, still a soldier who lost his head in the Civil War, is lopping off heads in an attempt to find his own. There is more to it than that, but I won’t give too much away.


Brom Van Brunt, played by Casper Van Dien, is also a much different character. He still acts like the village bad ass, but isn’t conceited about it like the other films. One of the best scenes is when he faces off against the Headless Horseman as the horseman continues to try and walk away to the woods, business as usual.


The legend continues to be retold and even inspired a TV show where Ichabod Crane somehow awakens in 2013 after beheading the horseman in the past. This legend will continue to inspire our current and future culture as a figure of Halloween that will never die.

Keep Exploring
The Knightscope K7 Robocop droid
RoboCop Begins as a Droid
%d bloggers like this: