And now a look at one of Disney's scariest tales with their take on Washington Irving's classic story about a schoolmaster who has a terrifying encounter! Paired in its recording with the story of Mr. Toad, this tale opens with narration from the great Bing Crosby. He sets things up in the charming but somewhat foreboding glen Sleepy Hollow near Tarry Town, when Manhattan was just a market town. It got a new inhabitant one day in Ichabod Crane, who was tall and exceedingly lanky, resembling a scarecrow walking around. In town was the group of "Sleepy Hollow Boys," led by Brom Bones. Though a prankster, Brom never intended harm with his jokes and was actually well-respected and considered a hero of the town. Voiced by Crosby, Brom begins the first song of the film, with the town folk wondering about the arrival of the odd Ichabod, whom Crosby also voices. Ichabod came into town as the new schoolmaster. He was firm, but always tried to stay on good terms with students, especially those whose mothers cooked well. Ichabod loves food so much, in fact, that he writes down who the best cooks are while pulling food out of strange places. He also has choir classes scheduled, to both bolster the town's culture and his own income. The women he teaches are head over heels for him, but Brom gets a laugh from getting a dog to howl as Ichabod performs. The prank doesn't bother Ichabod, who firmly focuses on his own proceedings rather than anything else, until the arrival of Baltus van Tassel and his daughter Katrina. Since Baltus is the richest farmer around and Katrina is exceedingly beautiful and kind, the men in town are instantly smitten, including Ichabod and Brom. We see in another musical moment from Crosby talking about how great Katrina is, though he also mentions that she seems to be vain and a flirt, as to her there's always another romance to start. Smitten with Katrina, Ichabod becomes lax at the school imagining marrying the woman and profiting heavily from the farm. He realizes Baltus would also be in the way, then shrugs the thought off, remembering that Baltus will eventually be gone. Despite a slew of admirers, Ichabod is confident he can overcome anyone, except Brom, who had both Katrina's interest and skepticism. Despite Ichabod's odd appearance, he catches her attention as well, due to his willingness to vie for her affections against Brom, who scared others away. Ichabod persists in spite of Brom's trickery, but with time his continued pursuit of Katrina got under Brom's skin. With no dialogue for a time, we see Brom become irritated as Ichabod repeatedly gets lucky and seems to slide past all his attempts to woo Katrina. He can't even punch the schoolmaster when he tries, as he doesn't want to offend the watching Katrina, and Ichabod escapes when he's distracted. Seemingly enjoying the feud, Katrina invites both men to a party at the van Tassel farm, adding "P.S. Please come" to Ichabod's letter. The excited Ichabod prepares for the party, sure that Katrina had chosen him, and rides into the night on a lame horse he borrowed, Gunpowder. The van Tassels were known to throw great parties, and as Ichabod prided himself on his dancing, Brom is forced to watch, again outmatched, while the schoolmaster dances with Katrina and simultaneously impresses Baltus. Brom notices a lone woman nearby, and as he is disgusted, he realizes he can use her to his advantage. This leads to himself and Ichabod then repeatedly dumping the excited woman off on each other to raucously dance. When he gets stuck with the woman, Brom manages to toss her into a side room. He opens a trapdoor to the cellar for Ichabod to fall in, but the woman's return results in his own slip. With the night drawing later and Ichabod's popularity on the rise, Brom realizes that he'll likely have to concede his defeat. Baltus soon calls on his guests to share ghostly tales, however, and as Brom knows Ichabod is superstitious, even seeing him toss some spilled salt over his shoulder, he sees a chance to make a comeback. He steps up in front of everyone and talks about the numerous ghoulish creatures out there, with other partygoers adding to his descriptions. Brom sings about how there are many creatures, but the Headless Horseman is the worst, scaring Ichabod further to Katrina's amusement. He hops around as the horseman as the others note that the Horseman rides alone and others don't like him. The Horseman wants to swap his flaming pumpkin head for another person's, and apparently he's not picky and can't be reasoned with. Brom claims he saw the Horseman the year prior, and rather than stop, he rode for the nearby covered bridge, which the Horseman is unable to cross. He therefore urges everyone, especially Ichabod, to make for the bridge as fast as possible, as the Horseman resides in the wooded hollow leading to Sleepy Hollow. With the party over, the movie then turns to Ichabod's journey home, which, fueled by Brom's story, turns into a frightening mess for Ichabod. This story from Washington Irving is one of the great American classics, for good reason, and this dark adaptation from Disney is perfect for Halloween.
Much of the movie is like Crosby's statement about Sleepy Hollow itself at the start: quiet, yet foreboding. Throughout much of the story, there is little true action. Sure, Ichabod and Brom get into their scuffles, but there is a lighthearted air to it all, especially since Brom was described as not meaning anything malicious in his pranks, although of course he gets rougher as Ichabod succeeds with Karina. Despite this, there is a somewhat unnerving underlying feeling, especially as Brom does become more hostile with Ichabod. The locations name, "Sleepy Hollow," already has a somewhat macabre feel to it, and being isolated from other towns by the woods gives creepy potential. This all bubbles over at the party, where Brom's idea to overcome Ichabod's efforts leads to a rather frightening tale about the dedicated and terrifying Horseman. Considering beliefs and superstitions people have held before, like the witch hunt days where women were accused of witchcraft for anything, a tale persisting of a horseman's headless ghost riding around could be believed. In the original story, the Horseman is described as being the ghost of a Hessian soldier from the Revolutionary War. A great thing about adapting such a story over time is that the characters can easily follow with this belief, and have it be that he simply persisted over time, or update it, as in Scooby Doo's The Headless Horseman of Halloween, where the Horseman was stated to be the ghost of a Civil War soldier. No matter which method you take, the Horseman is a classic ghostly foe who strikes fear into viewers' hearts. Considering he's a ghost, there's not really a conventional way to hurt him, and according to Brom and the others, he won't stop unless you cross the bridge. This is a typical belief in superstition, that unholy supernatural creatures, like witches, vampires, and ghosts, are unable to cross running water. According to tvtropes.com, running water, like salt and garlic, is often considered to have purifying powers, and symbolically, water is a source of life, and therefore deters the undead. There can be a catch with this, as sometimes bridges, like Brom mentioned, cannot be crossed either, and other times they can't. This becomes a point later on in the climax of the story. The idea of your only solace being a single section of running water with a covered bridge makes the Horseman more terrifying, since there's apparently no other way to stop him, and there's only the one path for Ichabod to get home. In other areas, the animation is splendid in this special, as would be expected from Disney, and has the great voice talent of Bing Crosby for songs, narration, and both Ichabod and Brom. There is also some incredible work at the end of the movie, as the slight noise of Ichabod's attempt to stay calm on the ride home is pierced with a chilling sound. Keeping it to such a minimal voice cast allows Crosby's voice to shine, as well as showcasing the art and animation to tell the story physically. Disney's The Legend of Sleepy Hollow came out in 1949, and it has aged incredibly well, standing the test of time as a terrifying entry in the Disney archives.
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