Deep Dive Disney: Wes Looks at The Legend of Sleepy Hollow

Welcome back everyone, to Deep Dive Disney and our two part look at The Adventures of Ichabod and Mr. Toad, the good part this time. The Legend of Sleepy Hollow is a rarity among the films we’ll be covering as it’s one of the few adapted Disney stories where I was very familiar with the source material prior to my initial viewing. I’ve always really enjoyed Washington Irving’s story. It’s one of the quintessential ghost stories of American literature and I always appreciated Ichabod Crane as one of the few noteworthy American literary characters from my home state of Connecticut. When I initially viewed the film at age thirteen, right on the cusp of being “too old” for Disney movies, I actually really enjoyed it and even found it a little creepy. I re-watched it for the first time since this past Halloween and have found it has since quickly risen in the ranks of my favorite Disney films of all time. I mean it, this short is not only beautifully animated with great music and haunting visuals, one can also see its influence all over later, more well-known Disney productions. Take our introduction to Ichabod Crane, strolling through town, nose in a book while all the townsfolk sing an upbeat song about how strange he is? That’s almost the exact same introduction we get for Belle in Beauty and the Beast. Speaking of Beauty and the Beast, one can certainly see the beginnings of what would become the villainous Gaston in Brom Bones. And take one look at Katrina Van Tassel and tell me she’s not a dead ringer for Cinderella, whose own film would be released the following year. It’s an absolutely wonderful work and I can’t wait to get into it. So, where were we? Well, after The Wind and The Willows segment concludes, singer Bing Crosby takes over narration duties and introduces us to Ichabod Crane and the town of Sleepy Hollow. While Crosby was known for having a soothing voice and his music often sounded very relaxing, which is not what one would typically expect for a ghost story, his silky tones surprisingly work well for this. Anyway, let’s meet our protagonist.

Main Character:

First and foremost, Ichabod’s design is perfect. Disney somehow captured the character exactly how I’d always pictured him in my mind, long before I knew this film existed. Tall, skinny, big ears, long pointy nose, everything. I also enjoy how the new schoolmaster of Sleepy Hollow is clearly an odd guy, but embraces it wholeheartedly, strolling through the town with total confidence. Weird looking by all accounts but still a total lady’s man. Impossibly skinny but eats like a living garbage disposal. Nowhere near as strong as Brom Bones but thwarts him at every turn. He’s a pretty cool character. However, he’s also kind of a scumbag in several regards. For example, during the scene where he’s daydreaming about Katrina, we see that his desires for her are not entirely based on love, but also on money. There’s even a bit where he basically fantasizes about Katrina’s father dying so he can inherit her vast fortune. He’s not a jerk on the same level as Toad, but that’s still not cool. Still, Ichabod’s ultimate weakness is his belief in superstition, allowing Brom to easily put the fear of the horseman into him long before they come face to um… not… face. Speaking of, let’s talk about ol’ Headless.

Villain:

Many of you will recall that Headless Horseman was ranked fairly high on my list of the Top 20 Disney Villains, considering the fact that he has significantly less scream time than his contemporaries. After re-watching this film yet again, I still stand by that decision one hundred percent. According to the origins of the character, the Headless Horseman was a Hessian, part of a group of German mercenary soldiers that the British employed during the Revolutionary War, who was decapitated by an American Cannonball who haunts the forest of Sleepy Hollow looking for a new head and wielding a flaming Jack-O-Lantern as a temporary replacement. In Irish Folklore, the Horseman is even darker, portrayed as a demonic fairy who uses a whip made out of a human spine! Jesus! Imagine what Disney would have done with that. Either way, the Horseman is one scary dude. The buildup to this big bad is insane, something we’ll discuss once we get to the Dark Disney Factor, but once the monster shows up, he does not disappoint. He doesn’t speak, nor does the horseman plot or scheme. You know exactly what he wants, and as the song says, you can’t reason with a Headless Man. You ever have that dream where something’s chasing you and no matter how hard you try, you can never really seem to get away? The Horseman reminds a lot of that. The Horseman is absolutely terrifying, with a laugh that will send a cold shiver down your spine and a relentless pursuit of Ichabod. A nice touch is how the background turns red every time Headless is on screen, something not as easy to animate as one may think, especially in the 40’s. To make things even more terrifying, by all accounts, The Horseman succeeds since Ichabod is never seen again after their encounter. I also should probably address the fact that The Horseman may have just been Brom Bones in disguise, something heavily implied but never actually confirmed in the original story. While I cannot speak to the intent of Washington Irving, in the Disney version, I say no way in hell. Not only are there lists of reasons that this version of the Horseman and this version of Brom cannot be the same person, there’s also the scene where Ichabod stares down the Horseman’s neck hole to consider. We don’t see what Ichabod actually saw, but whatever it was, it horrified more than it ever possibly could if it was just Brom Bones in there. But speaking of Brom, let’s get to our next segment.

Side Characters:

Let’s start with Brom Bones. Much in contrast to how Ichabod is kind of a jerk despite being the film’s protagonist, Brom, despite being an antagonist to Ichabod and the clear prototype for the unapologetically vile Gaston, is actually not really that bad a guy. Sure, he’s a bit of a prankster, but to quote Bing Crosby’s narration, there’s “No Malice in his Mischief” and by all accounts, the townsfolk see him as a hero. He only goes after Ichabod because they both happen to be courting Katrina, and, for all we know, Brom could suspect Ichabod’s less than pure intentions and could be trying to protect the lovely Ms. Van Tassel. In truth, while no saint, Brom really doesn’t do anything overtly villainous in the film, unless of course you subscribe to the theory that he was the Horseman all along, which I do not.

Moving on, let’s discuss Katrina Van Tassel. I get a sense that Katrina is not exactly the wide eyed innocent she may appear to be. From my perspective, she’s kind of an instigator, seeming to enjoy it when men fight over her, especially when someone like Ichabod, who actually poses a threat to Brom Bones comes along. She enjoys being the object of everyone’s affection and desire and doesn’t try to hide it. She can even be a little manipulative at times. This is all conveyed without a single line of dialogue. Very well done.

Songs:

Naturally, all of the songs in this film are handled by our narrator, Mr. Bing Crosby. I’ve always enjoyed Crosby’s music and while again, it can seem out of place for a ghost story such as this, the songs are still all top-notch, even if Katrina’s song sounds eerily similar to “It’s Beginning to Look a Lot Like Christmas.” Still, Ichabod’s introductory song is impossibly catchy, I’ve found myself whistling it for the past week. I would even argue it’s better than the song this scene would later inspire forty plus years later in Beauty & The Beast. However, the real greatest song in the film is the one Brom Bones uses to hype up the Headless Horseman. And yeah, it’s appropriately creepy and accomplishes its goal of scaring the hell out of Ichabod. It’s also pretty damned catchy and conjures up plenty of creep imagery. You gotta love it. It’s kind of a shame that these songs don’t get counted amongst the Disney Classics that often.

Memorable Scenes:

Don’t worry, we’ll talk about THAT scene in a little bit, but let’s discuss my other favorite scene, the one in which Brom and Ichabod quarrel over Katrina. Honestly, this scene is hilarious and loaded with some of the funniest slapstick I’ve seen in a Disney Movie. I love how Brom gets increasingly frustrated that everything seems to go Ichabod’s way, and even though he can probably kick the crap out of Ichabod, the schoolmaster still thwarts him at every turn, often to hilarious effect. The whole scene plays like an old Coyote and Roadrunner cartoon and I absolutely love it.

Story:

Not much to say here that we haven’t already discussed or will be discussing momentarily. The story is a classic of American Gothic literature and Disney captures it perfectly. What else is there to say?

The Dark Disney Factor:

Yes, the moment you’ve all been waiting for. It’s time to discuss one of the most well done and intentionally scary scenes in Disney history. Ichabod’s ride through the forest and subsequent encounter with the Headless Horseman. Let’s do a play by play, shall we? As Bing Crosby’s narration tells us that it’s the very witching hour of night, Ichabod, already on edge following Brom’s story, starts making his way through the allegedly haunted forest. Hesitant to enter the woods, Ichabod whistles to keep his spirits up, but clearly to no avail. Even the slightest breeze or noise causes the schoolmaster to flinch in fear, the whistling noise from his lips becoming increasingly difficult to produce the further he ventures into the dark forest. The clouds appear as hands covering up the moon as the entrance to the forest disappears behind the trees as if the woods are closing in on the schoolmaster. Foreboding music kicks in as Ichabod’s anxiety visibly increases. A gust of wind frightens Ichabod, causing him to try and get his horse to move faster, leading him right into a jump scare with a terrifying specter… that turns out to just be an ominously shaped tree and two fireflies. Now things get especially creepy as the crickets chirping begins to sound like a warning to Ichabod. An owl’s hooting sounds like the word “Doom.” A bullfrog croaks the Horseman’s name. All the while, Ichabod is not drenched in a cold sweat. The music grows more and more intense as the shape of the trees seem to grow even more menacing and the cacophony of ominous noises reaches a fever pitch. A crow flies down in front of Ichabod cawing “Beware” prompting the schoolmaster to increase the speed of his horse to a fast gallop. Hoofbeats are heard, but much to the utter horror of Ichabod, his own horse remains stationary, meaning only one thing, the Horseman is coming. Desperately, Ichabod tries to get his horse to move, but it won’t budge. Ichabod, as well as the audience, are lulled into a false sense of security when the “hoofbeats” are revealed to have been little more than reeds blowing against a log in the wind. So relieved and amused by what he’d been afraid of is our Ichabod that he erupts into hysterical laughter so infectious that even the horse joins in, and then, a third, more sinister laugh is heard, causing all that anxiety and terror that had just been alleviated to return with a vengeance. And there, standing on top of the hill, is the Headless Horseman himself in all his nightmarish glory. This scene and the ensuing chase are among the best ever produced by Disney. The tension is built effectively, the imagery is appropriately haunting, and when the time comes to reveal the big monster, it delivers and then some. I tip my hat to anyone and everyone involved the making of this scene. Bravo Disney, bravo.

The Legend of Sleepy Hollow is one of my favorite bits of Animation Disney has ever produced and why is not hard to discern. Great song, top-notch animation, memorable characters and one of the scariest and best scenes that Disney has ever produced. This film is a credit to the story it’s based on and I cannot praise it enough. Next time, we get back to something a bit more traditionally Disney as we look at Cinderella.