8 Best Adaptations Of The Legend Of Sleepy Hollow You Should Watch

There are few American folktales with the staying power of "The Legend of Sleepy Hollow." Written by Washington Irving, the original ghost story was first published in 1819 along with Irving's other famous work, "Rip Van Winkle," as a part of "The Sketch Book of Geoffrey Crayon, Gent." It wouldn't take long before the story of Ichabod Crane and the Headless Horseman would become a part of the greater American consciousness, and in just over 100 years, the first silent film adaptation titled "The Headless Horseman" was released.

Due to its spooky themes "The Legend of Sleepy Hollow" has remained a part of our popular culture. The Headless Horseman has become synonymous with the greater Halloween tradition, and the tale has been continuously adapted to fit various formats and genres while entertaining audiences of all ages.

Of all the adaptations out there (and there are many), there are some that are inherently better than others. Whether animated musicals, TV shows, or feature films, new and creative versions of "The Legend of Sleepy Hollow" will continue to find an audience. Here are the best adaptations of Washington Irving's literary classic.

The Adventures of Ichabod and Mr. Toad (1949)

The original animated adaptation of "The Legend of Sleepy Hollow," this Disney feature is two stories bundled into one. Contrary to the title, Ichabod Crane and Mr. Toad don't go on a journey together, but "The Adventures of Ichabod and Mr. Toad" still manages to be loads of fun as both Washington Irving's classic folktale and Kenneth Grahame's "The Wind In The Willows" are brought to life through animation. An RKO Radio Pictures production, "The Adventures of Ichabod and Mr. Toad" is the only Disney movie to star Hollywood icons Basil Rathbone and Bing Crosby.

Legendary crooner Bing Crosby lent his exceptional voice to this production as the narrator of "The Legend of Sleepy Hollow" portion. While "The Wind In The Willows" half of the movie only features two songs — one of them being "Auld Lang Syne" — "The Legend of Sleepy Hollow" contains three, each performed by Crosby opposite Billy Bletcher, who was best known for voicing the villainous Pete in the Mickey Mouse shorts. Bletcher used his infamous cackle to play the Headless Horseman.

There's a lot to love about Disney's adaptation, though the beautiful animation takes the cake. While both parts of "The Adventures of Ichabod and Mr. Toad" have been released separately, make no mistake, it's worth viewing them together.

The Legend of Sleepy Hollow (1980)

Jeff Goldblum may not seem like an obvious first choice to play Ichabod, but he makes incredible sense. Not only does Goldblum give off the perfect nerdy vibe for the character, but he also looks like Washington Irving's lanky schoolmaster. Although the 1980 "Legend of Sleepy Hollow" television film is somewhat dated, it was the definitive live-action version for many until Tim Burton's "Sleepy Hollow" was released in the late 1990s, and some fans still prefer it.

Although the original story is set in a small New York village, "The Legend of Sleepy Hollow" was filmed in the snowy landscape of Park City, Utah, but that's not the only big departure from the original story. This time around, Ichabod ends up with Katrina Van Tassel (played by Meg Foster) in the end, with Brom Bones finding love with an original character named Thelma Dumkey (Laura Campbell). As in the original story, the Headless Horseman doesn't appear much until the very end, but thankfully Ichabod Crane delights in his Goldblum-ish way.

If you're a classic television fan who loves Jeff Goldblum and made-for-TV movies, then "The Legend of Sleepy Hollow" is the film for you. Plus, Dick Butkus as Brom Bones is choice casting that brings a new level of intensity to the already intense character.

The Real Ghostbusters: The Headless Motorcyclist (1987)

When you need help dealing with a centuries-old ghost, who ya gonna call? That's right, the Ghostbusters took on an '80s version of Headless Horseman called the Headless Motorcyclist in an episode of "The Real Ghostbusters" animated series. After Peter Venkman is framed for a ghostly assassination attempt, the Ghostbusters are forced to track down the Headless Motorcyclist and capture him to save Ichabod Crane's descendant from death — and Peter's reputation and career. As Kate Crane explains to the ghost hunters all about her family's curse, we learn that the headless specter changes over time, adapting to modern ways and culture.

Besides the exciting '80s animation that looks just as good today, watching the Ghostbusters battle the Headless Horseman may be something out of a fever dream, but it's a good one. "The Headless Motorcyclist" is not the best-known episode of "The Real Ghostbusters," but it's one of the better adaptations of Irving's tale, even if it deviates pretty far from the source material. If anyone could take on the Headless Horseman and live, it would be the Ghostbusters.

"The Headless Motorcyclist" takes the original concept behind "The Legend of Sleepy Hollow" and mashes it with "Ghostbusters" in a way that keeps the story fresh and the ghosts scary. Besides Ichabod Crane himself, they're the most natural fit to fight this headless spirit!

The Tale of the Midnight Ride (1994)

The original "Are You Afraid Of The Dark?" was a horror anthology series not unlike "Goosebumps" that aired on Nickelodeon and ran from 1990 until 1996 before a two-season revival in the late '90s and a reboot that debuted in 2019. If you're looking for a less intense version of the story to share with your pre-teens, then this might be the version for you. Kicking off the third season, "The Tale of the Midnight Ride" is a very '90s adaptation that swaps out Ichabod Crane for a teen named Ian Matthews (Tighe Swanson) who's just trying to fit in with the kids in his new high school — the difference being, all the kids know the local legend for themselves.

As in the original "Legend of Sleepy Hollow," Ian is sent by his bully into the woods on Halloween night, this time to find the Headless Horseman's everlasting pumpkin. Where Ichabod went right, Ian chooses to go left, and what awaits him is something very strange indeed. Between encountering the ghost of Ichabod Crane and the real Headless Horseman, Ian and Katie — a Katrina van Tassel stand-in played by Rachel Wilson — go through a lot in this dated version of the tale.

As Ian and Katie are forced to play out the legend for themselves, they answer the age-old question with a resounding "yes." They are afraid of the dark...

Sleepy Hollow (1999)

Of all the high-profile filmmakers to direct an adaptation of "The Legend of Sleepy Hollow," none make more sense than the gothic Tim Burton himself. In "Sleepy Hollow," an R-rated live-action adaptation of Washington Irving's story, Tim Burton casts Johnny Depp as Ichabod Crane, a constable in this version, opposite Casper Van Dien as Brom Bones, Christina Ricci as Katrina Van Tassel, Christopher Lee as New York City's Burgomaster, and a combination of Christopher Walken and Ray Park as the Headless Horseman. Unlike many other interpretations of this story, Burton emphasizes the horror elements and leans into his familiar gothic themes to tell this strange story.

"Heads will roll" as you enjoy this peculiar version of the tale that relies heavily on supernatural horrors and Burton-ish charm to sell you on the Headless Horseman's reign of terror. Depp's Ichabod Crane is fascinating as well, and while admittedly very different from the version of the character we read about in Irving's short story, he manages to be a hero worth following into the darkest depths of Sleepy Hollow. Complete with a powerful score by Danny Elfman and a solid script by "Se7en" writer Andrew Kevin Walker, "Sleepy Hollow" reigns supreme as a big-budget Burton horror movie.

If gothic horrors are your thing, then Tim Burton's "Sleepy Hollow" is the adaptation for you. It may deviate from Washington Irving's original work, but it does so with style and class.

The Smurfs: The Legend of Smurfy Hollow (2013)

If all of these adaptations of "The Legend of Sleepy Hollow" are a bit too spooky for you or your kids, then don't be afraid to check out "The Smurfs: The Legend of Smurfy Hollow!" This 22-minute short film expertly combines the 3D animation of "The Smurfs" movies with the traditional animation of the original cartoon. Set sometime after the second live-action "Smurfs" movie, this animated "Smurfy Hollow" celebrates the annual Smurfberry Hunt as the rivalry between Brainy Smurf (voiced by Fred Armisen) and Gutsy Smurf(voiced by Alan Cumming) comes to a head and turns out to be a bit spookier than they'd hoped.

Admittedly, "The Legend of Smurfy Hollow" doesn't follow the original story much at all, but it's still pretty entertaining and is a good time for audiences of all ages. There may not be an Ichabod Crane here, though Brainy would surely be the Ichabod stand-in, but there is a Headless Horseman who haunts the Smurfs and their nemesis Gargamel. Well, there's sort of a Headless Horseman, but we won't spoil the ending for you.

The most kid-friendly of this bunch of "Sleepy Hollow" adaptations, "The Smurfs: The Legend of Smurfy Hollow" may just be the short film your family needs to ease them into Washington Irving's chilling story.

Sleepy Hollow (2013-2017)

Certainly the most liberal of all the "Legend of Sleepy Hollow" adaptations, the Fox series "Sleepy Hollow" combines Washington Irving's original short story (and elements of his other best-known work "Rip Van Winkle") with American history and biblical prophecy to tell an apocalyptic tale that surprisingly works a lot better on the screen than it sounds on paper. The series stars Tom Mison as a more heroic Ichabod Crane and Nicole Beharie as 21st-century newcomer, Sheriff's Lt. Abbie Mills, who are revealed to be the Two Witnesses of the Book of Revelation tasked with facing the Seven Tribulations that threaten to destroy the world.

Over the course of 62 episodes, Crane and his companions face off against demons, witches, wendigos, golems, and of course the Headless Horseman — who turns out to be the biblical Fourth Horseman of Death — as they fight to save not just the town of Sleepy Hollow but the entire world. While the series departs from the original, its ability to expand on Irving's original works and add greater supernatural flair show a sort of originality that many of the other more direct adaptations fail to find.

With four seasons to binge, "Sleepy Hollow" is lots of fun and teters on the line between being your average police procedural and a supernatural thrill ride. Plus, they even did a two-part crossover with "Bones," which is one of the strangest bits on the show.

Headless: A Sleepy Hollow Story (2022)

The most recent "Sleepy Hollow" adaptation, "Headless: A Sleepy Hollow Story" is a ten-part series by Shipwrecked Comedy that takes the classic folktale in a completely different (and modern) direction. Following a young socially awkward science teacher named Ichabod Crane (Sean Persaud, who co-created the series with his sister Sinead Persaud) who moves to the village of Sleepy Hollow. In need of a roommate, Ichabod bunks with the Headless Horseman. With the help of the town witch, Matilda, the Horseman is transformed into various historical characters, each destined to ruin Ichabod's life.

Along for the ride are Kat Van Tassel, the mayor's daughter and Ichabod's love interest, and Brom Bones, the local gym teacher and a frenemy to the young science teacher. As the series continues, things quickly get out of hand as it leans heavily into comedy but with some dramatic twists. "Headless" is a great time and one of Shipwreck's best productions to date. You can watch "Headless" for free on YouTube.

If you're not really into children's adaptations or Tim Burton, and you aren't sure you want to commit to a multi-season adaptation of "The Legend of Sleepy Hollow," then look no further than "Headless: A Sleepy Hollow Story." The episodes go by faster than Ichabod on Gunpowder, and it's a remarkably clever spin on the traditional tale.