Legends of Sleepy Hollow

I thought about saving this one for October, but since we’ve already established our love for watching Halloween movies at times other than Halloween, and since you will need some time to track down any of these films you might want to see, I decided to post it early.

Washington Irving’s The Legend of Sleep Hollow is one of my all-time favorite books. I read it several times a year, once in October and other times whenever I want life to feel like it does in October. The Legend of Sleepy Hollow is not really a ghost story. The Headless Horseman only appears in the last five minutes of the hour-long read, and even then he is clearly not a ghost but Brom Bones in disguise. Nonetheless, its climax occurs on Halloween and so it is indeliably linked with Halloween. In fact, the Horseman is one of the most Halloweenish characters there ever could be.

And this Halloweenish character isn’t limited to the printed page. He has appeared in TV shows and films as well, chasing the superstitious schoolmaster Ichabod Crane across both the silver and the smaller screen. Here are a few of the movies he has appeared in:


Walt Disney’s The Legend Of Sleepy Hollow: narrated by Bing Crosby, this version of the tale is undeniably the version; it is not only the closest to the original but also the most enjoyable in its own right. I first saw it in middle school and have loved it ever since. The end chase is included in Disney’s Halloween Treat and a version is paired with Mr. Toad’s Wild Ride to create The Adventures of Ichabod and Mr. Toad. It’s solo version, which has a slightly different opening from the Mr. Toad version, is the best. Unfortunately, no DVD exists for this version. You’ll have to get it in one of its many VHS incarnations. I suggest the Walt Disney Home Video version which comes in the white clamshell box. Don’t get the “Mini-Classics” version, which is just an awkward rip from The Adventures of Ichabod and Mr. Toad and begins with Bing’s narration in the middle of a sentence.

Shelley Duvall’s Tall Tales And Legends – The Legend Of Sleepy Hollow: a live action version staring Ed Begley Jr and Beverly D’Angelo. It is a fairly loose adaptation of the story and is more like a stage play than a film. The general structure remains the same (Ichabod arrives, flirts with Katrina, goes to the party, and meets the Horseman), but lots of additional scenes are added. I found it kind of boring. The characters were just about right, though.


The Legend Of Sleepy Hollow: another live action version. This one stars Jeff Goldblum, Meg Foster, and Dick Butkus. It, too, follows the general structure of the story, but it makes a lot of changes a long the way. It is set in winter rather than autumn, which is a pretty significant and unforgiveable change as far as I’m concerned. It also introduces a lot of new characters and is more drama/mystery than ghost story. Goldblum (who here is the least Goldblumy that I’ve ever seen him) is a fairly good Crane, though he is unfortunately skeptical of ghosts rather than superstitious as he is in the book.

Hallmark’s The Legend Of Sleepy Hollow: Yet another live action version. This one was made in 1999, but it looks like it is much older. It again follows the general structure of the story, but it greatly alters the characters. Katrina comes out as a much more sensible person than she should be, Ichabod is still laughable but for the wrong reasons, and Brom doesn’t seem as threatening as in the book. There are lots of added scenes here as well, most of which are dialogue. One scene that I found kind of amusing (and I imagine Claymation Werewolf would as well) included a lengthy discussion of the “savageries” of Ohio. There is also an Ichabod dance scene which ends with Ichabod stricking a pose and making an expression very familiar to that of Silence of the Lambs’ Buffalo Bill.

One great thing about this version is that it incorporates a lot of lines from the book, including some from the epilogue, which itself is absent from a lot of the e-versions of the book .

Sleepy Hollow: Tim Burton’s live action version of the story starring Johnny Deep and Christina Ricci. This Sleepy Hollow is not an adaptation of the book as much as it is an original story that borrows some of the book’s elements. For that reason, it really can’t be compared to the others. It is enjoyable, though, and the visual aesthetic is some of Burton’s best.

Night of the Headless Horseman: a computer-animated version with the voices of William H. Macy, Mark Hamill, Clancy Brown, Luke Perry, and Tia Carrera. It is a better adaptation than any of the live-action ones (probably because it is shorter and so has less time to fill). It is also much more gory. The computer animation in this version is early computer animation and has the surreal quality that computer animation had at that time, i.e., the characters don’t really seem to be saying what they are saying. That aside, it does have a strong Halloween feel and is worth a watch.

And there are a host of other movies that bring the Sleepy Hollow mythos into modern times or reference it in some way, such as The Hollow, Sleepy Hollow High, Headless Horseman, The Haunted Pumpkin of Sleepy Hollow, and Curse of the Headless Horseman.

None of these versions match the book, of course. The book is a masterpiece, filled will little snippets of life in those times and little revelations of the lovable stupidity of men that remains constant in all times. No film version can possibly match that. But if you get tired of Halloween movies this October, you can always turn to any of these Legends. After all, Halloween belongs to the Headless Horseman and Washington Irving just as much as it belongs to Michael Myers and John Carpenter.


Doug is a child of the 80s who was raised in Ohio and is now living the life of oblivion in the bay area of California.

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