Home Cinema It’s been 20 years since this Halloween icon was in the cinema

It’s been 20 years since this Halloween icon was in the cinema

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It’s been 20 years since this Halloween icon was in the cinema


When Halloween rolls around, there’s usually a pipeline of movies and stories that people flock to to get into the spirit of the season. Horror fans tend to keep the spirit alive all year round. However, Halloween has not always been viewed favorably in all communities across the United States. The festival’s connection to witches and other supposed dark forces has caused some groups to avoid participating in the festival. But there is something about Halloween that has made it a recognized and beloved holiday in the United States.




One of the stories that tends to resurface at the spookiest time of year is Washington Irving’s “The Legend of Sleepy Hollow.” The legend itself has inspired Disney and Tim Burton films. First published in 1820, the story features the infamous character, the Headless Horseman, and his unfortunate victim, Ichabod Crane. And it harks back to an era in early Dutch America that makes it a unique part of the American pantheon of folklore.


Washington Irving is best known for “The Legend of Sleepy Hollow” and “Rip Van Winkle”

Tim Burton's Sleepy Hollow Has an Incredible Villain in the Form of a Headless Horseman


Irving was an early 19th century writer, essayist, biographer, historian, and diplomat. He is widely known in literary circles and among the American people, not only as the author of “Sleepy Hollow”, but also of “Rip Van Winkle”. The latter is a short story about a Dutch-American villager who falls asleep and wakes up 20 years later after the American Revolution has occurred and overtaken him. The story was published in a collection of stories titled The sketchbook of Geoffrey Crayon, Ghent. Geoffrey Crayon was one of several pseudonyms used by Irving for his publications. Others included Diedrich Knickerbocker and Jonathan Oldstyle.

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“Sleepy Hollow” was part of the same store collection as “Rip Van Winkle”. This was the first time American audiences would experience the Headless Horseman. It’s around Halloween that the story tends to resurface in popular media. Yet when “Sleepy Hollow” was written, Halloween was not a mainstay of the American holiday season like it is today. And the story represents America at the time of its publication very well. Specifically, set against the backdrop of Dutch America and making the Headless Horseman a fallen Hessian (1917 edition) – a German soldier serving the British during the American Revolution.

TV Features Based on “Sleepy Hollow”

“The Headless Horseman of Halloween” (1976) • Animated short film

The Legend of Sleepy Hollow (1980) • Live action film

The Legend of Sleepy Hollow (1985) • Live-action film

The Legend of Sleepy Hollow (1999) • Live-action film

The hollow (2004) • Live-action film

Sleepy Hollow (2013) • Live-action series

Headless: A Sleepy Hollow Story (2013) • Live Web Series


The plot and setting of the spooky tale of “Sleepy Hollow” are simple. The story takes place near an old Dutch settlement known as Tarry Town, in a glen called Sleepy Hollow, circa 1790. Ichabod Crane is a stranger who arrives in town from Connecticut as a new schoolmaster. He attempts to woo a wealthy farmer’s daughter, Katrina Von Tassel, much to the dismay of a local rival, Abraham “Brom Bones” Van Brunt. Brom convinces Ichabod that there is some truth to the local legend of the Headless Horseman, said to be the ghost of a Hessian soldier shot in the head by a cannonball during the Revolutionary War. The story ends with Ichabod being chased by the Headless Horseman after a party in town one evening, which ends with the schoolmaster disappearing.


Whether or not Ichabod succumbed to the Headless Horseman as a true specter is unclear from the text. Irving suggests, by means of a squashed pumpkin near the site of Ichabod’s disappearance, that it may have been Brom who chased him out of town in disguise. But the mystery makes the story just as haunting. In a 2005 opinion piece for the New York Times, Andrew Burstein examined how this “curious quality…made it an instant hit with adults and children alike – when it appeared in 1820”. Further adding, “We don’t quite identify with Ichabod because there is something un-American about him, and he reads a little too seriously into the Puritan teachings of the pompous cleric Cotton Mather.” What Burstein essentially points out is how the story captures the shifting prism of Americanism over the years and the American public’s relationship with Halloween and “darker” ideals.

The images feature Ichabod Crane and two townspeople from The Adventures of Ichabod and Mr. Toad.


One of potentially the best known and most recognized versions of “The Legend Sleepy Hollow” was made by Disney. It appeared as an animated short in the feature film The Adventures of Ichabod and Mr. Toad (1949). Bing Crosby narrated the sequence and thus serves as the voice of all the characters. The short film was associated with The wind and the willows, narrated by Basil Rathbone, with a number of other actors voicing the characters of Mole, Ratty, Angus MacBadger and J. Thaddeus Toad, Esq. Oddly enough, Sleepy Hollow was originally destined be a full-fledged feature film. But this project was finally abandoned when its cost was considered too high after the Second World War.


It is curious to consider what a feature film is Sleepy Hollow what it was like in Walt Disney’s time. Disney’s tendency to not go too dark with its material seems to fluctuate, but it was certainly less prevalent in Walt’s time. The “Night on Bald Mountain” sequence from Fantasy and even certain scenes from Snow White and the Seven Dwarfs (1937) and Pinocchio (1940) might not be seen in today’s sugary bubblegum Disney films. Even if the films like The black cauldron (1985) and The Hunchback of Notre Dame (1996) showed that Disney was still perfectly capable of following Walt. Of all the live-action remakes that Disney has offered since 2015, Sleepy Hollow would definitely be a potentially popular choice, especially with the release of Hocus Pocus 3 on the horizon. And it would give the studio a chance to give the story the feature-length treatment as originally planned.


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Disney was not the first to attempt to bring this famous American legend to the screen. The first known film version of “The Legend of Sleepy Hollow” was a 1992 silent film starring observational comedian Will Rogers as Ichabod Crane. Renowned Disney animator and co-creator of Mickey Mouse, Ub Iwerks, do an animated short film titled The Headless Horseman in 1934, preceding Disney’s own version. This was the first time that Iwerks revealed his invention of the multiplane camera for animation. This new technique was “capable of filming through layers of animated backgrounds moving forward or backward.” And Walt Disney Studios would use this technique for many years. Outside of television, the next full film treatment of “Sleepy Hollow” wouldn’t arrive until the late 1990s.


Tim Burton produced the last true adaptation of Sleepy Hollow in 1999

In 1999, Tim Burton took on the task of creating another live-action version of “Sleepy Hollow”. Sleepy Hollow starred Johnny Depp, Christina Ricci, Miranda Richardson, Michael Gambon, Christopher Lee and Christopher Walken. The film features Ichabod as a New York City police officer sent to Sleepy Hollow to investigate the series of murders that led there, leading to the decapitation of the victims. Ichabod’s new role turns the story into a dark murder mystery and adds a compelling extra layer to the plot. Depp said of his view of Ichabod, “I always thought of Ichabod as a very delicate and fragile person who was perhaps a little too in touch with his feminine side, like a scared little girl.” Another distinct difference from the source material is that this version ends with Ichabod and Katrina leaving Sleepy Hollow together at the end and returning to New York.


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It’s been over 20 years since Burton Sleepy Hollow was released in theaters, and another version has yet to surface. Surprising in the age of remakes and reboots. There was a television series that aired from 2013 to 2017, loosely inspired by the tale. Sleepy Hollow was a supernatural drama that aired on Fox and ran for four seasons before its eventual cancellation. The show involves time travel, which brings Ichabod to the present day to help a local sheriff find the Headless Horseman, who is once again on the loose in Sleepy Hollow. There have actually been discussions about a reboot Sleepy Hollow as a Paramount+ series. Yet since Burton, no one seems to be working on another feature film adaptation. As enthusiasm for Halloween continues to lose momentum among the American public, perhaps it’s time to revisit this favorite American terror story.


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