The Legend of Sleepy Hollow Adaptations: Part 1

The Legend of Sleepy Hollow by Washington Irving is one of  the most popular stories to come out of the early 1800's in America. The tale has endured the test of time and is mainly associated with the holiday of Halloween due to the supernatural aspect of the story. With any popular book, there are film and television adaptations. There just happen to be a lot of adaptations, all starting in 1922 with the silent film version. Not just limited to movie length adaptations, the story has also been done in television episodes, some doing a faithful recreation, and some just using it as a jumping off point. I thought it would be fun to go through all the different versions of the tale I could find and see how much they differ from each other and from the source material. Before I start on the adaptations themselves, I'll give a short summary of the book for reference. 

The Legend of Sleepy Hollow concerns a Connecticut school teacher who moves to a small town in New York called Sleepy Hollow in the year 1790. Ichabod becomes the town's new schoolmaster and is known as being strict with his students, though not too strict as to not warrant a welcome invitation to their houses for dinner. Ichabod is tall, thin, and though very learned is also extremely superstitious. He lives with various farmers during his tenure at Sleepy Hollow and also teaches choir to the women of the town. Ichabod soon meets Katrina Van Tassel, a young woman known for her beauty and wealth. Her father, Baltus Van Tassel runs the largest farm in the town and therefore is well-to-do. Katrina has many suitors, but it is Abraham Van Brunt, also known as Brom Bones, a rough and tumble man with a reputation as being mischievous, who has laid claim to the wealthy heiress. Ichabod and Brom compete for Katrina, but Brom cannot seem to get rid of Ichabod like the other suitors, as he cannot fight him outright, and Ichabod is unwavering where others have had more sense and left Katrina alone. Ichabod sees Katrina as a way of improving his station and thinks to himself that once he marries her he will forget everything about being a school teacher and even look down on the lot. Brom, realizing that Ichabod is superstitious, plays various pranks on him, including tearing up his school house in order to make Ichabod think that witches had held a meeting there. Katrina appears to be playing the two against each other on purpose. Things come to a head when Katrina invites Ichabod to a harvest party at her home. Ichabod dances with Katrina while Brom looks on with jealousy. Ichabod then goes and listens to spooky tales by the fire, which eventually turns into the whole group talking about Sleepy Hollow's most famous ghost, The Headless Horseman. Brom even chimes in, saying that he raced the Horseman for a bowl of punch but the Horseman disappeared once Brom went over the church bridge. Ichabod stays after the party in order to propose to Katrina, but it apparently doesn't go well, as he leaves the party devastated. He takes the horse he borrowed from Hans Van Ripper, the person whom he is currently staying with, and makes the journey back through the dark woods. The ghost stories get to him while he's riding home and he starts to fear everything is out to get him. He rides on until he sees a stranger on a horse riding nearby. He doesn't panic at first because he cannot see who it is and tries to talk to the stranger. It's only once the figure is backlit by the night sky that Ichabod sees that it is the dreaded Headless Horseman. The Horseman chases Ichabod all through the woods until they get close to the church bridge. The Horseman throws its head at Ichabod and Ichabod falls to the ground. The next morning, Hans Van Ripper doesn't see Ichabod at all and the schoolmaster is absent from the school house. Eventually the people of Sleepy Hollow find Ichabod's hat on the ground near the bridge with a smashed pumpkin nearby. The townsfolk all believe that Ichabod has been carried off by the Headless Horseman. Brom and Katrina marry, and Brom is seen having a knowing look when the Headless Horseman incident is brought up in conversation. Word came back to Sleepy Hollow that Ichabod Crane was alive and well back up north where he started a law practice. Some believed this, but most continued to believe that the Headless Horseman had finally found a head. The schoolhouse was abandoned and folks say that you can hear the old schoolmaster singing his hymns nearby. 

The Headless Horseman (1922)

The earliest version of the Sleepy Hollow story, it doesn't stray too far from the book's premise. Ichabod is his usual self, though maybe a little more proud and arrogant. He flaunts his intellect over the people of Sleepy Hollow, who he considers country bumpkins. In some versions of the story Ichabod is looked at with fascination because he is an outsider, some he is looked on with derision for the very same reason. This version gives you a little of both. In one of the additions to the tale, Brom convinces the townsfolk that Ichabod is a witch-doctor who put a spell on a young boy. Ichabod is nearly tarred and feathered by the townsfolk, but is luckily saved by Baltus Van Tassel, who has taken a liking to the unusual pedagogue. This version of the tale ends with no ambiguity like the short story does. Brom is revealed to have been the Headless Horseman after he runs Ichabod out of town. There are some unusual parts, too. When Ichabod asks Katrina to marry him, the words on the screen make it look like she says yes, but the reaction makes it look like she said no. Not sure if there was some missing footage or what. There are two different ways you see the Headless Horseman: a solid body that ends up being Brom, and a ghostly looking one when the movie introduces the Horseman. I like the double exposure effect they used for the horseman as it adds some great spookiness to the movie. Not my favorite version of the tale, but it is interesting to see how they tackled the tale in the early days of film. This version is available on Amazon Prime. 

The Adventures of Ichabod and Mr. Toad (1949)

This adaption is the first animated one, and comes from Disney. I watched this version many, many times over the years, though mostly the last third of the film. To me, this version is the best that there has ever been. It's short, but not too short, and hits on all the main plot points. The characters don't talk, you just get the narration from Bing Crosby. That itself would push this near the top, but the film also has some genuinely funny moments and an exciting climax. All the songs that Crosby sing are great, but especially The Headless Horseman. There are a lot of great spooky moments throughout, from the Van Tassel party, to Ichabod's late night ride on Gunpowder. The chase scene is one of the best set pieces in Disney animation history, and really drives home that Ichabod is in real danger. With most of the Sleepy Hollow adaptations, you see Ichabod ride away screaming for a minute and then get hit in the head by a pumpkin. The Horseman merely scares and chases him but not much else. In this version, the Horseman is full on trying to cut off Ichabod's head with a sword. It still culminates with Ichabod getting hit with a pumpkin, but this time it's a flaming jack-o-lantern. Love it. In terms of characterizations, they all fit into the classic molds. Ichabod looks just like he is described in the book and shows off several times how superstitious he is. Katrina is fair and it's made pretty obvious that she is purposefully playing the men against each other. Brom is an oaf and a bully, and that's about all that is said about him. It think that while the identity of the Horseman is still left ambiguous, I still feel like it's supposed to be an actual ghost. Besides the Horseman trying to outright kill Ichabod, Ichabod gets a good look down the Horseman's collar and I feel like he would most likely be able to tell if it was a person under there. Brom may be jealous, but he is never portrayed as murderous, just a practical joker. So it seems a stretch to say that he was trying to murder Ichabod. The animation is also the best of all the other animated adaptations of the short story by far. I credit Mary Blair's magnificent backgrounds and concept art. This is about the only adaption that hits the autumn time aesthetic hard, whereas most of the others seem stuck in a never ending bleakness. Highly recommend this as a kid's first introduction to The Legend of Sleepy Hollow, as it covers everything pretty well story-wise, and I would say it's not the scariest version of the tale. This is available to watch on Disney Plus.

Tales of Washington Irving (1970)

An Australian animated TV special that includes the story of Rip Van Winkle and The Legend of Sleepy Hollow, both being Irving tales. The animation is what you would expect from the late 60's, early 70's, so it's not too bad. Katrina is about the only one that looks a little weird. I think it's the stilted way that she talks, too. Ichabod sounds an awful lot like Paul Lynde (he did a lot of voices for Hanna-Barbera) so that's a little distracting, but it fits the character well. Ichabod is very superstitious and mentions that witches used to use Sleepy Hollow as a meeting place, along with his belief that the Headless Horseman is real, because so many people have claimed to see him. Katrina is much less coquettish than in the short story. She bristles at Brom's affections and says to her friends that she would like someone with some intellect, like Ichabod Crane. One unusual part of this adaptation is that Sleepy Hollow is not considered where the people live, but instead the woods and countryside are Sleepy Hollow. I guess the people live in Tarrytown? Though Katrina seems to like Ichabod throughout the story, she ultimately rebuffs him at her family's party, and probably one of the harshest ways I've seen. She laughs right in his face, asking why would she want to give up all she has to live in poverty with the schoolmaster. He tries to say that he could take over the farm, but she laughs at this too, saying that he may be a good schoolmaster, he wouldn't be any good at farming. The ending leaves the identity of the horseman ambigious, and Katrina marries Brom. The school house falls into disrepair and they say Ichabod's ghost haunts the area. This ending is probably as close as they come to the end of the book, as it's the only one that mentions the schoolhouse being abandoned. The characterization of Katrina is very odd for this adaption. She really seems to favor Ichabod until he asks her to marry him, and though she claims to detest Brom, she marries him. Not a bad cartoon, but not nearly as good as Disney's. You can watch this one on Youtube. 

The Legend of Sleepy Hollow (1972)

This is a very short adaptation of the tale, mostly known for it's unusual visuals and for the narration of John Carradine. This version is extremely 70's, as you can tell by the music, unique animation style, and the use of color. There is not a lot of detail with the backgrounds, it's mostly just one backdrop of color, which permeates the rest of the scene, though the characters are often a different color to make them stand out. In terms of the story, it hits the main beats, including Brom playing pranks on Ichabod and Katrina saying no to Ichabod's proposal. They even have Ichabod not run immediately upon seeing a figure in the woods who ends up being the Headless Horseman. This one is worth a look if you don't mind the overtly 70's aesthetic. This is available to watch on Youtube. 

The Scooby Doo Show: The Headless Horseman of Halloween (1976)

Scooby and the gang, plus Scooby-Dum, are at a costume party at Crane Manor. Beth Crane explains to the gang that Ichabod is her great-great-grandfather. Beth's Aunt Gertrude is hosting the party and shows off her diamond necklace. The Headless Horseman shows up and scares all the guests away. The gang attempt to solve the mystery of the Headless Horseman and why he's come back to haunt the Crane's again. Gertrude's nephew, Elwood, mentions that the diamond necklace she wears is cursed and of she gives them to him to put in the bank, this will all stop. He leaves with the diamonds and is quickly "killed" by the Headless Horseman. Now the Horseman is riding around with Elwood's head on. The gang eventually catch the "ghost" and reveal it to be Elwood (BUM BUM BUMMMMMM). Elwood's company had gone bankrupt so he was going to use to diamonds to start a new life in another country. He had to keep the façade of the Horseman alive so the ghost would be blamed for the diamond necklace's disappearance. All in all, not a bad Scooby Doo episode. Not the best, but it's from The Scooby Doo Show, so it's never going to be the same as Scooby Doo, Where Are You? As with most Scooby Doo villains, Elwood's Headless Horseman is not that threatening. The episode gives a short recap of The Legend of Sleepy Hollow, but there's not much else there. This begins the trope of not doing a straight adaptation of Sleepy Hollow but using a descendant to tell a new story in modern times. This is available to watch on HBO Max.

 The Legend of Sleepy Hollow (1980)

Jeff Goldblum plays Ichabod Crane in this TV movie adaption of the Sleepy Hollow story. Goldblum's Ichabod is different from other incarnations in most ways. While still brainy, as you would imagine from a school teacher, he lacks the belief in superstitions and ghosts, at least at first. There's a few new characters in this version: Fritz Vanderhoof, an older man that tries to get Ichabod to believe in ghosts, his widowed daughter Thelma Dumkey who is chasing after Brom Bones, and Brom's dim-witted best friend, Frederick Dutcher. 

Ichabod comes to Sleepy Hollow and quickly hears from Mr. Vanderhoof that ghosts haunt this town and that each of the previous school teachers went funny and disappeared in the night. Winthrop Palmer, one of the most unlucky school teachers, was said to have been driven into the river to his death by the Headless Horseman. Ichabod doesn't entertain such nonsense, but as the story goes on, he's not so sure there isn't something supernatural going on at Sleepy Hollow. Ichabod falls in love with Katrina, whom Brom has claimed but has yet to make a move officially. Seems Brom struggles with commitment issues! Mr. Vanderhoof tries to set up Ichabod with his widowed daughter, but she has eyes for Brom. It's one big mess all capped off by appearances by the ghost of Winthrop Palmer. He mostly harasses Ichabod throughout the story, before finally coming to him face-to-face and telling him that he seeks revenge on Brom for trying to scare him off, and on the Headless Horseman who drove him off the cliffs into the river. Ichabod isn't quite sure if Palmer really is a ghost or not, but he starts to believe more than before in the supernatural when he runs into the Headless Horseman outside his school house. He starts "acting funny" in the eyes of the town, talking of the Headless Horseman and Palmer's ghost coming to him, and though he had been making strides in winning Katrina's heart, it's all for naught when her father deems him to be unfit for her. Ichabod's classroom is destroyed and he believes it to be ghosts, so he brings Squire Van Tassel (Balthus's title) back with him, only to find it's back to normal. This doesn't help his case at all. Ichabod gets in a tussle with Brom at the Van Tassel's winter ball, and he is banished from the house by Squire Van Tassel. He rides home, dejected, not knowing what awaits him. Meanwhile, back at the Van Tassel's, Brom and his buddy Dutcher plan to scare Ichabod away for good by dressing up as the Horseman again. Palmer, wanting revenge on Brom, is about to jump out at them from a barn, but gets tangled up in a rope instead. He is soon found by Mr. Van Tassel, who realizes that Ichabod wasn't funny in the head. Palmer had been pretending to be a ghost the whole time in order to get his revenge on Brom. Ichabod is on his way home when he runs into Brom's Headless Horseman. The real Horseman joins the fray and Brom runs away, right into Mr. Vanderhoof and his daughter. They realize that it has been Brom pretending to be the Horseman this whole time, and threaten to tell the whole town if he doesn't marry Thelma. Brom begrudgingly agrees. Ichabod, now believing that the Horseman is none other than Palmer, chases him into the town square, back to the Van Tassel's house. The Horseman disappears past the house and Ichabod calls out for Squire Van Tassel. Squire Van Tassel reveals that he found Palmer in his barn and that Ichabod is not crazy after all. He allows Ichabod to marry Katrina, though Ichabod almost ruins it by mentioning that he had just been chasing Palmer here, so he couldn't have been in the barn. Katrina kisses him to shut him up, and they all go inside to celebrate the engagement. 

As you could probably tell, there were quite a few differences between this version and most of the others. Added characters aside, there's also the fact that it is made plain that the Headless Horseman is real. Katrina actually marries Ichabod in the end, changing the more depressing ending of the traditional story. Brom doesn't make out that bad, though. He gets a girl, but just not the one he had wanted. There are plenty of story beats that fit with the original story, though mostly to do with what Brom does to harass Ichabod. In general, I like this version better than most of the other TV versions because it tries to do something different, like Burton's Sleepy Hollow does. It doesn't go that far out of the realm of the story, but just adds some extra pieces to make the story a bit more interesting. Jeff Goldblum is always gold, even in an early role like this. You do have a few other well-known actors (at the time) in the movie, namely Meg Foster as Katrina, Dick Butkus as Brom, and Paul Sand as Dutcher. Michael Ruud plays Winthrop Palmer and he's by far the most hammy of them all. He pretends to be a ghost by making the most clichéd ghost wails and laughs that you have ever heard. It's too funny not to love. Butkus's Brom is a dumb oaf like most other Brom's, but this version has a moustache, so he is infinitely more interesting and out of place. All in all I like this version a lot, though I know the quality isn't exactly top notch. It reminds me of watching late night movies on the VCR as a kid. It just has that soft, grainy quality to it. It's on Youtube if you're interested in watching it yourself. 

Shelly Duvall's Tall Tales and Legends: The Legend of Sleepy Hollow (1985)

The Legend of Sleepy Hollow was the first episode of Shelly Duvall's second anthology series. In this version we meet Doffue Von Tassel, Katrina's uncle and the narrator of our tale. Doffue is a part of the story but breaks the fourth wall to talk to the audience. Everything about this adaption is over the top, acting wise. Ed Begley Jr. plays Ichabod Crane with a manic energy, taking the description of Ichabod being fearful and superstitious to the extreme. I'm pretty sure he yelps and screams more than he talks. Tim Thomerson plays Brom Bones and he is also chewing the scenery, acting like a cross between Gaston and Johnny Bravo. There is definitely more humor inserted into this version than any of the others, which is apparent by the animated performances. While the characterizations are the same, the legend surrounding the Headless Horseman have changed. The pesky phantom instead of a Hessian soldier was a highwayman who lost his head by a sword instead of a cannonball. There is no mention of a bridge to cross, just that a Headless spirit roams the woods of Sleepy Hollow looking for a new head. The tale ends with a definitive answer that it was Brom that scared Ichabod off with a Headless Horseman costume. While that is only mildly surprising, the real twist is that Brom himself becomes the victim of the Headless Horseman the night after Halloween. It seems that Ichabod may have gotten some justice in the end. Another adaption that you can find on Youtube.

Are You Afraid of the Dark: The Tale of the Midnight Ride (1994)

This version centers not so much on Ichabod and the Headless Horseman, but a middle-schooler named Ian. Ian is new to Sleepy Hollow and is having a hard time making friends due to him trying way too hard. While the school is setting up for a Halloween party, Ian runs into Katie, who he immediately falls for. Of course, Katie is dating a bully named Brad and Brad doesn't take too kindly to Ian making nice with his girlfriend. At the dance, Ian and Brad get into a confrontation that leads to Brad telling Ian he must go to the Bridge of Souls to recover a pumpkin, as it is a town tradition. This version of the Headless Horseman story differs as it centers in Ichabod taking a wrong turn and not making it to the Bridge of Souls before the Headless Horseman gets him. Once he goes and gets the pumpkin, the Headless Horseman arrives and chases him until Ian falls and begs for his life. Of course it ends up being Brad and all the kids come out of the woods and mock Ian. Katie decides to stay with Ian, mad that Brad has embarrassed Ian. While walking back to the dance the couple run into a ghostly man on horseback asking which way to the Bridge of Souls. They tell the ghost the right way and the specter identifies himself as Ichabod Crane before disappearing into the fog. They get back to the school and run into the real Headless Horseman who chases them because they changed the story. Brad gets his comeuppance when he, still wearing the Horseman costume, gets scared by the real Horseman and falls down backwards. Ian and Katie run all the way back to the bridge where Ian leads it across and the Horseman bursts into flames. The couple see Ichabod once more at the bridge who tells them he is lost and will go back to the fork and go his original way, thus setting the story straight. The two tired teenagers head back home, happy to no longer be in danger and look forward to their new relationship.

Besides using The Legend Of Sleepy Hollow as a backdrop, the main story itself draws parallels, namely in the love triangle. Ian, Katie, and Brad are all plays on Sleepy Hollow's Ichabod, Katrina, and Brom. There are obvious differences in how the love triangle plays out, as Katie ends up with Ian in the end instead of with Brad. Katie also doesn't lead Ian on just to make Brad jealous as Katrina does to Ichabod. The show had to add the part about Ichabod taking a wrong turn so they could come up with a way for the kids to change the story. The episode itself is just OK. I think I never noticed how Canadian the accents are in this show when I was a kid, or maybe this episode was extra egregious thanks to how many times Ian says "sorry". Ian is not likable at all. Everybody knew a kid like this growing up, or you were that kid sometimes without even knowing it. A lot of unearned confidence in this kid. The twists on the Sleepy Hollow story are fun and I like stories about towns with spooky traditions, real or otherwise. In the end, it's not a go-to if you are looking for a story about Sleepy Hollow and is definitely not one of the best Are You Afraid of the Dark episodes. I'll make a list of those when I get around to watching them all over again. You can watch this episode on Youtube.