Long, long ago, before New York became the crazed, crowded, liberal, epicenter of art, culture and yuppies, there was a little town known as Sleepy Hollow, which was just that: a sleepy town where the residents sit around snoozing. The only life of the party was a brash young gentleman named Brom Bones, who although fancied himself to be a bruiser and a troublemaker, he was still seen as a gentleman and a town hero. That is, until one fateful day there came a new man in town: an awkward, lanky man with a misshapen head and long, pointy nose in a book, simply known as Ichabod Crane. He quickly drew the attention of everyone in town-man and horse-as they had never seen his kind before. Yeah, something tells me the people in this town don't read. Ichabod is the new schoolteacher, and he runs a tight ship. However, he's willing to forego any infractions in exchange for dinner invites. You see, not only does Ichabod adore free meals, he's also quite the ladies' man. One such lady really caught his fancy: Katrina Van Tassell, only daughter of the richest farmer in the county. She would have the men lining up to catch a glimpse and flirt with her. Despite being a tart, she's got the men swooning and even worshiping the very ground she walks on. So, in addition to Sleepy Hollow being a boring, dead-end burg, it must also be the bachelor's capital of America... either that, or these men are really gonna be in dutch with their wives. As for Ichabod, he spends days on end, fantasizing about Katrina, and about her rich daddy's farm. Is Ichabod a gold-digger, or is he genuinely interested in the prettiest and most sought-after maiden in town? You make the call. But yeah, he is a gold-digger. Looking to inherit all that sweet land when Farmer Daddy kicks off. Stirring up some pretty bad karma there, Ichy. Eh, what's the worst that could happen? He lose his head? Ha ha.
However, someone else was interested in the fair Katrina: ol' Brom Bones, who seems to go from town hero to bully in this scene, chasing off those other desperate men to have Katrina to himself, but he has a formidable adversary to contend with in Ichabod Crane. Back and forth, he and Brom perform acts of chivalry, trying to outdo each other, but only end up embarrassing themselves. After all, Brom could've just been a man and let Ichabod win this round, but all's fair in love and war, I guess. After that, the plucky new schoolteacher finds himself invited to old man Van Tassell's annual Halloween night ball, where he delights in the free food, kissing up to Mr. V.T., and dancing with Katrina, while Brom Bones just sits around and sulks, as his only alternative was dancing with a fat chick. His attempts at changing partners always fell flat. However, fortune may soon work in his favor, as he notices another little quirk about Ichabod: he's superstitious. Knowing he'd believe a ghost story hook, line and sinker, Brom tells, or rather, sings about a mysterious and nefarious Headless Horseman: a cursed demonic presence who wanders the wood one night a year, looking to get head... I mean, get a new head. He tells the only solace is to make it across the bridge, as the Headless Horseman can't cross it for some reason. Well, I dunno, maybe ol' Brom Bones is full of hooey and probably just sang that catchy song for kicks. Either way, Ichabod's ride home through the dark, spooky woods was very unsettling. Just the tiniest sounds and whistling of the wind made his knobby knees wobble. But I don't blame him, these are the scariest woods in the whole world. Even the Blair Witch would be terrified of this place. And worse, it seemed like all these creatures were mocking him. Suddenly, his horse comes to an unexpected stop, but Ichabod still hears the sound of hoof beats. Could it be? Naw, it was just some cattails tapping against a log. Ha. He and his horse have a good laugh, as there was nothing to be afraid of... OH MY GOD! It's the Headless Horseman! With a terrifying cackle, he raises his razor sharp sword and takes a swipe at Ichabod's head, so he and the horse haul ass out of there. But that evil being is close behind them, cackling and brandishing his sword. After riding topsy-turvy through the woods, they see the bridge in the distance, knowing freedom was a short distance away. But as Ichabod and his horse cross the bridge, the Headless Horseman tosses them a parting gift: a flaming pumpkin. By daybreak, all that remained at the scene were Ichabod's hat and a shattered pumpkin. So in the end, Brom Bones got the girl, and as far as Ichabod, some think he got away, settled down and started a family, but everyone else knows the truth, that he was "spirited away" by the Headless Horseman.
There have been many incarnations of the Legend of Sleepy Hollow, most notably Tim Burton's, but most people are familiar with the Disney version. The Headless Horseman has been hailed one of the scariest villains ever to appear in a Disney film. There is some speculation as to who he really was, as he wasn't seen or mentioned until that climactic chase. Personally, I buy into the theory that Brom Bones was the Horseman, trying to either kill Ichabod or run him out of town. The narrator says he was a practical joker, and we all saw how jealous he was of Ichabod, and how he'd been made a fool of in front of everybody in town. Jealousy can drive a man to do some pretty crazy things, and it wouldn't be entirely beneath him to resort to foul play in order to get his way. If this is the case, then he's a Disney villain who not only got away with his evil deeds, but also gets the girl in the end. Pretty brazen for Disney to go that route, even if it is how the book ended, as the Hays Office often demanded a happy ending. All that aside, this was a fantastic short film, narrated and performed brilliantly by Bing Crosby. Rich with detail and the splendor that Disney's animation never fails to deliver and perfect to watch around Halloween, I definitely recommend The Legend of Sleepy Hollow. And remember, kids, it's only a cartoon... right?