Page To Screen: The Legend of Sleepy Hollow

Washington Irving at around the time The Sketch Book was published. (Wikipedia)

One of the most iconic tales of American literature is The Legend of Sleepy Hollow. Written by Washington Irving and originally published in 1820 as part of his Sketch Book, this story of ill-fated schoolteacher Ichabod Crane never fails to chill. It also never fails to find new life in various media.

For those who aren’t familiar with it, the plot of Sleepy Hollow is as follows: City-dweller Ichabod Crane takes a job as schoolmaster in the village of Sleepy Hollow. He also takes a liking to Katrina Van Tassel, the rich daughter of a local farmer, as does Abraham Van Brunt, known around town as Brom Bones. The two of them attempt to win her by outdoing each other in romantic manliness. What’s ironic is these two couldn’t be more different. Brom is as hunky as they come, while Ichabod looks like, in Irving’s words, “some scarecrow eloped from a cornfield.”

In between wooing Katrina and sparring with Brom, Ichabod gives music lessons to the locals, whom he considers backwoods hicks. He’s also quite happy to be invited to various homes for dinner, as he likes to eat.

First edition of The Sketch Book, which included “The Legend of Sleepy Hollow,” published initially as a series between 1819 and 1820. (Library of Congress)

Lest this all seem too placid, Sleepy Hollow has a secret. It’s said to be bewitched, and everyone who lives there is equally bewitched. To top it all off, a Headless Horseman is said to haunt the woods by the churchyard. He was once a Hessian thug hired by the British to wreak havoc on the Continental Army, which he does until his head is blown off by a cannon ball. Ever since, he gallops through the woods at night looking for another head to replace his own.

Ichabod is incredibly superstitious, and on Halloween night, he goes to a party at the Van Tassel farm, where the Headless Horseman story scares him stiff. On his way through the woods after the party, Ichabod encounters the mysterious Hessian and faces the ride of his life.

Washington Irving’s tale has very little dialogue and reads like an oral history. It does have a slight grain of truth in it. Written through the eyes of a fictional character, Diedrich Knickerbocker, the story is set in the village formerly known as Tarrytown, which is on the Hudson in upstate New York. Ichabod, Brom, and Katrina were possibly inspired by real people, and they are all buried in the Old Dutch Burial Ground in Sleepy Hollow.

“Sleepy Hollow” has been adapted dozens of times in both audio and video formats, but since this is a “Page To Screen,” we’ll be taking a peek at some of the films based on Irving’s story.

The Headless Horseman (1922)


This was one of the first instances in which Irving’s story was brought to the screen. Starring Will Rogers as Ichabod and Lois Meredith as Katrina, the film quotes directly from Irving’s text and follows the storyline pretty closely, except for a brief bit in which Ichabod is accused of witchcraft and put in the stocks. He’s saved from being burned at the stake by one of his schoolboys who confesses Brom put him up to falsely accusing his teacher.

This brief interlude was obviously intended to fill out the story and doesn’t really add much in the way of tension, but it’s still kind of satisfying to see Brom apologize to Ichabod. It’s also fun to see Rogers striding around in his tricorn and breeches, enjoying himself hugely, although it feels a little odd to see him without his trademark lasso or polo mallet. The film was shot in the real Sleepy Hollow and has excellent special effects, chief among them being the double exposure used to portray the Hessian. Watch the film here.

The Adventures of Ichabod and Mr. Toad (1949)

The Girls In the Back Row

Ah yes, the peerless Disney version, starring Bing Crosby and only Bing Crosby as the narrator. This adaptation is a lot of fun, and it’s probably the most faithful of any filmed “Sleepy Hollow,” as it sticks to Irving’s original light-on-the-dialogue format. While dismissed by some as being too happy, the film does work in a certain amount of menace through changes in tone and the Horseman’s relentless pursuit of Ichabod.

The music is typical Bing-style crooning, which works nicely into Ichabod teaching music and provides effective continuity. Ichabod originally had to share title space with Mr. Toad of Wind In the Willows fame, but was later jettisoned as a re-release for TV in 1955. Seventy years later, Disney’s take on Irving is still a perennial classic. Watch a portion of the film here.

The Legend of Sleepy Hollow (1980)

Teleport City

Jeff Goldblum plays Ichabod, and Meg Foster is Katrina in this made-for-TV movie, and the quality is just about as high as one would expect. Read: It’s pretty bad. The dialogue is a mishmash of late eighteenth-century and late twentieth, and the pacing is rather clumsy. However, the film is not without its charms, as Goldblum wears the Ichabod role well, giving it a nervous awkwardness that really works.

What’s unusual about this telling of the story is that it’s set in the winter instead of the fall, and Ichabod’s fate isn’t sealed. He also isn’t alone in the woods when the Headless Horseman comes galloping through. What’s really unusual is Dick Butkus as Brom Bones. Watch the entire film here.

Murder, She Wrote (1987)


In the eleventh episode of Season Three, Angela is thrown into a Sleepy Hollow scenario, except that it takes place in Vermont. A schoolteacher named Dorian (Thom Bray) is trying to impress the father of Sarah (Karlene Crockett), the woman he loves, with his background, and he invites Jessica to visit for the weekend. Problem is, the whole town thinks she’s his mother, at least at first.

In a bit of swell novelty, the Brom Bones character, Nate Findley is played by one Barry Williams, and unlike other versions, Nate (Brom) is the one to be taken down by the supposed Hessian.

Wishbone (1997)

Google Play

This show was adorable. The dog was adorable. Its version of “Sleepy Hollow” was adorable, too, with the titular canine playing Ichabod. Broadcast in two parts on October 15, 1997, this take interspersed smelly socks and a scavenger hunt with classic Irving. It’s not at all scary, and it’s not meant to be, which is just fine. And there’s a healthy dose of slammin’ 90s fashion. Watch the episodes here.

The Night of the Headless Horseman (1999)


This TV special discards the mysterious and comical parts of Irving’s story and fully embraces the horror. The Hessian isn’t just a rumor; he’s a Sleepy Hollow fixture, ticking up his body count anytime a hapless person is foolish enough to be in the wrong place at the wrong time. There’s no question what happens to Ichabod on Halloween night, as Brom makes a deal with the Hessian, who later demands payment. The film features an all-star cast, including William H. Macy as Ichabod, Luke Perry as Brom Bones, Mark Hamill as Adrian Van Ripper, and Tia Carerre as Katrina.

What makes the film hilarious is the animation. It’s a combination of very, very early CGI and stop-motion, and most of it is rendered pretty strangely. Among other howlers, Katrina looks like she’s doing the Funky Chicken, and Brom’s derriere is rather, um, deep. Funniest of all is Ichabod Crane, who bears a remarkable resemblance to those James the Butler stands from the 1980s, only not as flat and wrinkly. Watch the film here.

Sleepy Hollow (1999)


Ichabod got a makeover in Tim Burton’s take on Irving’s story. He’s not lank and scarecrow-like. He’s not superstitious. Heck, he’s not even a schoolteacher. He’s Constable Crane, who is sent to Sleepy Hollow to investigate the mysterious beheadings. He rolls into town armed with some rather modern forensics methods and a trunkful of gadgets. Instead of a straightforward investigation, he finds a community full of secrets.

The R-rated film is a mix of mystery, horror, and Burton’s trademark quirkiness, with more than a few disembodied heads staring us in the face thoughout. It’s also rife with durable actors and actresses who have horror firmly in their sizeable wheelhouses. Sure, it doesn’t look much like the original story, but it’s a fun ride all the same. I’m thinking I’ll revisit this one in a full review someday.

The Haunted Pumpkin of Sleepy Hollow (2003)


Set in the present day, this cartoon follows two kids, Nick and Kate, who have to retrieve Irving’s original first edition after it’s been stolen. The thieves are of the bumbling, non-threatening variety who hide the book in a pumpkin. Rather improbably, the pumpkin becomes magical, sparking all kinds of keep-away games between the kids, the thieves and the Headless Horseman himself. Not to mention, there are a few friendly ghosts around to help out.

The show features a lot of Green Day-ish music and classic 2000s animation. My son was reminded of Liberty’s Kids when we watched it. He thought it was fun, but I thought it was a little weak. See the whole film here.

Sleepy Hollow (2013-2017)


Last and probably least is the Sleepy Hollow TV series, which ran for four seasons. Its premise is weak from the start, as it involves resurrecting Ichabod Crane (Tom Miso) to help solve a crime. Ahem. If that would be Ichabod as he apparently died in the story, it would mean he’d be headless. So yeah, that’s a problem, but why quibble? The series only used Irving as window-dressing anyway. Ichabod’s not a teacher in this version either. Instead the series focused mostly on eschatology and the occult, including Ichabod having made a deal with the devil. Heh. However, it also has fish-out-of-water Ichabod trying to adjust to the twenty-first centuty, which is sort of fun.

I’ll be honest, I never watched a full episode of Sleepy Hollow, and I honestly didn’t want to. There was nothing that grabbed me. My husband, who normally goes for this type of viewing fare, didn’t watch it either. However, I felt that it should be included as an example of the way Irving’s story is still a pervasive part of American culture. See a trailer here.

It’s not hard to say why we still find Irving’s tale intriguing. It has an underdog. It has a love triangle. It has mystery. It’s utterly charming. It brings a long-gone era to life as if it happened yesterday. It’s pretty safe to say there will be more adaptations of The Legend of Sleepy Hollow, and it will be interesting to see how others approach the story.

Another Origins post is on the way. Thanks for reading, all…

9 thoughts on “Page To Screen: The Legend of Sleepy Hollow

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.