Halloween Review: ‘The Legend of Sleepy Hollow’


During the 1940’s Walt Disney Productions was engaged in what has been dubbed by many the “package film era”. Thanks to the Second World War, the studio’s ability to make further big prestige pictures like Snow White and turn a profit of them had been hampered. This was hammered home after disappointing box office results from Pinocchio. With this obstacle Walt Disney and his collaborators opted to apply the grand scale artistry of animation to a series of shorts they could package together to sell to theaters. They ranged from wartime propaganda to travelogues and, as in the case of this 1949 production, short stories to show off the talent of the animators and entertain audiences. Packaged alongside an adaptation of the Wind in the Willows for the feature The Adventures of Ichabod and Mr. Toad, this retelling of Washington Irving’s The Legend of Sleepy Hollow has been a staple of Disney’s Halloween offering annually for years.

In the village of Sleepy Hollow, the always hungry Ichabod Crane takes over as the new schoolmaster. While the local women in this small town try to impress Crane, he only has eyes for Katrina, the daughter of the prominent Van Tassel family. The problem is Sleepy Hollow’s resident macho alpha male Brom already has a romantic attachment to her. In a move to intimidate the new school master, Brom invites Crane to the local Halloween party. It is here he theatrically recounts the tale of the Headless Horseman who stalks the forests every Halloween night searching for a new head. This leads to Ichabod’s journey home being filled with dread culminating with the beheaded undead Hessian himself chasing Ichabod through the night.

Even with the smaller pool of resources they had to work with with the Legend of Sleepy Hollow, directors Jack Kinney and Clyde Geronimi led their team into doing the same top notch job as would be expected from a full length picture. The combination if storytelling and animation is on par with Pinocchio and the other feature films of the era. Given the nature of the story, animators did not hesitate to delve into the scarier elements of Sleepy Hollow. Visually they gave it the same creepy Expressionistic flair as the Universal Monster and Val Lewton films of the era. The nightmarish woods and the Headless Horseman that stalks them are rendered to moody scary perfection. The fact that Ichabod Crane is so successfully portrayed as an awkward and lanky outsider, the threat at hand that much greater as we know he does not stand a chance. The scene where Brom regales the Halloween revelers with the Headless Horseman’s legend is truly a standout. Whereas most filmmakers would do this through flashback, the animators on Legend of Sleepy Hollow manage to make someone recounting through song and pantomime the tale absolutely captivating while still accomplishing what it needs to do from a story point of view.

If I do have a minor problem with this short film it is thew choice of crooner Bing Crosby as narrator. This is not to say he is bad at the role, he is perfectly serviceable and naturally nails the singing parts. But the “Swinging on a Star” singer does not necessarily have the kind of chilling voice to amplify the atmosphere. Considering horror favorite Basil Rathbone narrated Sleepy Hollow‘s sister production The Wind in the Willows. But his smooth voice does go along way in humanizing the protagonist of Ichabod Crane. The version of Crane we get here is certainly not the greatest of guys. He manipulates the village women into being his source of food and his motives for pursuing Katrina Van Tassel are incredibly shallow. But hearing his thoughts coming from the man who charmed us in Holiday Inn goes a long way in getting us behind Crane.

Due to the nature of Disney productions in this era, most of them works from the “package film era” has been forgotten. But the Legend of Sleepy Hollow has stood the test of time. Even as the company moves away from the scarier elements of their early works, this short has stood the test of time. On a trip to Disney World a few years ago I saw many references to the tale of the terrifying horseman without a noggin in the colonial America-theme Liberty Square. Unlike so many other Disney adaptations, this one actually sticks close to the original story taking few creative liberties (but the changing of the Horseman’s head from a standard pumpkin to a Jack o’ Lantern is a stroke of genius) meaning this was the introduction countless people have had to the works of Washington Irving. For those having to choose Halloween viewing for a family with a wide age range the Legend Sleepy Hollow proves to be the perfect choice. It is perfectly entertaining for adults, while still delivering just the right amount of scares for younger ones, balanced with enough humor for levity.