Rob Price
When thinking of Halloween, we often think of the modern-day horror icons, like Michael Meyers, but let’s not forget one of the originals, The Headless Horseman, from the 1820 short story by Washington Irving, which takes place in Sleepy Hollow, New York. The story has had many film and television adaptations, but the plot remains generally the same. Ichabod Crane, a lanky superstitious schoolmaster competes with Brom Van Brunt for the hand of the richest girl in town, Katrina Van Tassel. Ichabod is not physically intimidating, but well educated and well-liked by the women of Sleepy Hollow, where Brom is the rowdy town hero. After being frightened by the haunting tales told at by Brom at the Van Tassel harvest party, Ichabod begins his journey home, through a wooded area reputed to be haunted. Here he encounters a headless rider, a legendary Hessian trooper beheaded by a cannon ball during a Revolutionary War battle, who chases Ichabod towards the covered bridge which the malevolent spirit cannot cross. Although Ichabod makes it to the safe side of the bridge, he turns to see the horseman hurl his head, striking him and knocking him off his horse. In the morning, only the horse, a shattered jack-o-lantern and Ichabod’s hat are found. Irving leaves the story up to interpretation as to what actually happened to Ichabod. Some believe that the rider was Brom in disguise who through the Jack-o-lantern instead of a head, scaring Ichabod so bad that he shamefully ran from the town never to return, others believe that he was spirited away by supernatural forces.
The Headless Horseman (1922 silent film)
The first adaptation was a silent film starring Will Rogers, a popular actor at the time, who took the part against his normal type casting. In this version, Ichabod is generally disliked by the townsfolk due to his harsh and smallminded teaching approach.
The Adventures of Ichabod and Mr. Toad (1949 animated film)
This Disney produced anthology film featured a rendition a bit truer to the story, but with its own “looney toons” style treatment. The Legend of Sleepy Hollow segment was narrated by Bing Crosby who also voiced Ichabod. This was fully intended for children with a lot of physical humor and sight gags as well as some catchy musical tunes. This was entertaining for children, while teaching them a little bit about literature.
The Legend of Sleepy Hollow (1980 Television Movie)
Starring Jeff Goldblum as Ichabod and Meg Foster as Katrina, this television film is only loosely based on the short story and ends with Ichabod surviving his terrifying ride and returning to the Van Tassel residents and the horseman disappears back into the forest. In the original story, Katrina marries Brom, but in this version, Brom ends up marrying a different woman.
Sleepy Hollow (1999 Movie)
Probably the biggest budget production of the adaptations and also the biggest divergence from the story. Directed by Tim Burton and starring Johnny Depp and Christina Ricci, Ichabod is a police officer from New York city sent to investigate the strange decapitations of several town folk in Sleepy Hollow. The supernatural element is real and not just a legend, and the characters must discover who is controlling the reanimated body of the Hessian soldier played by Christopher Walken.
Sleepy Hollow (2013-2017 Television series
A television series that finds Ichabod Crane, after killing the Headless Horsman and dying in the battle himself, magically resurrected and transported to modern day Sleepy Hollow, where the Horseman has also returned. Crane is played by Tom Mison and works with Sherriff Abbie Mills played by Nicole Beharie to avert the end of times, as the Headless Horseman is Death, one of the legendary four horsemen of the apocalypse.
Other Appearances of the Headless Horseman
The Headless Horseman character has also appeared in several other movies that are not direct interpretations of the original story. In 2004, we got The Hollow a movie where a high school student finds out he is the descendant of Ichabod Crane and must work with his friends to stop the recently resurrected Headless Horseman. Similarly, in 2007 saw the Sci Fi Channel’s television movie, Headless Horseman, a modern-day teenage horror film, where the Horseman is a hung serial killer from the 19th century who rises every seven years to collect the heads of seven “youths”. Finally, our favorite blue woodland creatures, the Smurfs, gave us The Smurfs: The Legend of Smurfy Hollow in 2013, putting their own “smurfy” spin on the legend!
The classic image of a headless horseback rider with a jack-o-lantern for a head has scared people for centuries now and will hopefully continue to do so. All the stories listed above have put their own spin on the legend, embellishing the source material and making new legends helping to relate the story to modern audiences.