Sunday, October 1, 2023

Film Review: The Legend of Sleepy Hollow (Disney; 1949)

 "The Legend of Sleepy Hollow"

*** (out of ****)

Although this Disney animated adaptation of Washington Irving's "The Legend of Sleepy Hollow" (1949) is most often associated with Halloween, I believe a more interesting interpretation of this Disney movie would be as an examination on the Seven Deadly Sins.

Originally released under the title "The Adventures of Ichabod and Mr. Toad" - as an anthology movie adapting Irving's story and Kenneth Grahame's The Wind in the Willows, this is the second known movie adaptation of "Sleepy Hollow", coming after the silent movie, "The Headless Horseman" (1922) starring comedic wit Will Rogers. Disney would re-release this story as a stand alone VHS under the title "The Legend of Sleepy Hollow", which is the version I will be be reviewing.

At approximately 33 minutes "The Legend of Sleepy Hollow" is a rather slight movie that doesn't waste much time getting into the heart of Irving's famed story. It could have benefitted from an additional 10 minutes however to better establish its characters and plot developments. Instead this Disney adaptation tells Irving's story with a broad brush, hitting on the main points of the tale without going into the nitty-gritty details. Unfortunately, this may cause some viewers to lose sight of the themes Irving was working with.

In an absolute master stroke, Bing Crosby is cast as the movie's narrator, informing us of the treacherous legend that occurred in the quiet town of Sleepy Hollow back in 1790. The story begins with the arrival of a new schoolmaster, Ichabod Crane, a lanky and timid man with his face buried in a book. He is immediately a cause for suspicion from the male townsfolk including Brom Bones, the town's brute (who was undoubtedly the drawing inspiration for the character Gaston in "Beauty and the Beast" (1991) decades later). Perhaps interpreting his bookish ways for that of a smug, intellectual outsider and / or picking up on his weakness, Brom and his friends make Ichabod the butt of their pranks. And it is because of his weak nature Ichabod never retaliates, ignoring Brom's behavior.

Despite Ichabod's awkward physique the town's women take a liking to him. As a child this never made any sense to me and watching it again as an adult it remained equally as confusing. The interactions with the females provide an insight into Ichabod's real passion, an insatiable appetite for food. Presenting him practically as a glutton. Events take a turn when the wealthy daughter of Baltus von Tassel, Katrina, a young coquette, is introduced to the story. She has captured the eye of all the men in town especially Ichabod and Brom. "The Legend of Sleepy Hollow" now falls into that old predictable scenario of the girl having to choose between the tough guy jock and the kind-hearted weakling.


While hitting on the themes of masculinity, the movie is able to display humorous moments revolving around this premise. The best of these is a sequence where Brom and Ichabod both try to escort Katrina home after a day of shopping. The two men fight over which one of them will carry all of her packages. "Sleepy Hollow"  however has something else up its sleeve. Does Ichabod really love Katrina or does he simply lust after her beauty like the rest of the men? Ichabod we discover is in love with the idea of Katrina's wealth and the idea that he might inherit it one day if the two ever get married.

This leads to a problem I have with "Sleepy Hollow". None of the three main characters are likeable. It is an unusual move for a Disney movie not to have a hero. Katrina is exactly as described, a coquette - a flirtatious young woman merely interested in gaining the attention of men. She plays Ichabod and Brom against each other, igniting a jealous rage within Brom. I doubt any of these characters have any true feelings for each other. To Brom I suspect Katrina is a prize. He won the prettiest girl in town. To Katrina, she probably views Brom as the most masculine option in town and therefore Brom becomes her prize. The two most attractive people have found each other. And we already know Ichabod's motivation. 

This is what inspires me to believe "The Legend of Sleepy Hollow" is a parable of the Seven Deadly Sins. Between these three characters we eventually see all seven sins committed - Lust, Gluttony, Greed, Sloth, Wrath, Envy, and Pride. But unfortunately the movie doesn't have anything to say beyond this point. There is no moral to the story, another very unusual move on Disney's part.

In order to finally get the upper hand, Brom's last resort is to play on Ichabod's fears. In the original story, Ichabod is an admirer and firm believer of ghost stories. This aspect of Ichabod's personality is not emphasized here. During an annual Halloween party thrown by the van Tassel's, Brom tells the legend of the Headless Horseman - the spirit of a soldier who appears every Halloween night searching for a replacement. He warns everyone to beware on their ride home. Brom's plan works as Ichabod's imagination gets the best of him during his journey back home as every noise causes him to panic.

This creates an interesting dichotomy in the Ichabod character. He is supposed to be a learned man, he is the town's schoolmaster after all, and yet this man believes in ghost stories. This is a conflict between science and superstition. This theme isn't fully explored in this adaptation. Tim Burton would do a better job accentuating this facet of Ichabod's personality in his adaptation of the story in "Sleepy Hollow" (1999) with Johnny Depp as the lead character.


Ichabod's ride back home is probably the most famous part of Irving's story and this movie. It is because of this sequence the story is associated with Halloween. And this sequence is scary. As a child watching it, it would frighten me. It may still be able to scare younger viewers although I am somewhat doubtful given what children are apt to see in horror movies today.

What "The Legend of Sleepy Hollow" does surprisingly well is combine different genres so effortlessly. The movie balances elements of comedy, the musical, and horror. What is further so impressive is how it does all of this in such a short amount of time and effectively encapsulates the mood of those genres. The Headless Horseman sequence alone could have been its own story.

"The Legend of Sleepy Hollow" was of course made in the great cel animated tradition of some of Disney's best movies. Viewers should pay attention to the use of perspective, colors, rhythm, and value (lighting). Again, watch the Headless Horseman sequence for the best examples of this. Sadly this style of animation is a lost art with CGI now the dominate technique.

The men behind this movie - Clyde Geronimi, Jack Kinney, and James Algar were the same men behind Disney classics like "Pinocchio" (1940), "Dumbo" (1941), "Bambi" (1942), and "Cinderella" (1950).

If you are looking for something to show the little ones this Halloween, "The Legend of Sleepy Hollow" might be a good option. Children today don't seem to be able to enjoy animation like this I have noticed, using my nieces and nephews as examples. The children can somehow detect the movies are "old" and just that knowledge alone often makes them unwilling to watch something. It might be the adults that will get more enjoyment watching "Sleepy Hollow" for nostalgia's sake.

And it was nostalgia that lead me to write about "The Legend of Sleepy Hollow" in the first place. With the year long celebratory "year of me" - my celebration of my favorites artists and filmmakers in honor of my 40th birthday and the 15 anniversary of this blog - I thought October would cause a bit of a snag in the celebration. For nearly every October during these last 15 years I have dedicated the month to reviewing horror movies. Over the course of this time I have reviewed most of my favorite horror movies which didn't leave me many options to fulfill the "year of me" theme. 

"The Legend of Sleepy Hollow" is a fun, if slight story, that effortlessly mixes comedy, music, and horror all done to a perfect narration by Bing Crosby. The Headless Horseman sequence is a treasure to watch even though these are not the most likeable characters to spend time with.