The Legend of Sleepy Hollow is a Disney Halloween short that is based on a short story by Washington Irving. Narrated by Bing Crosby, it was originally part of the 1949 Disney package film The Adventures of Ichabod and Mr. Toad and later re-released as a separate featurette.
Plot[]
In October 1790, Ichabod Crane, a lanky, gluttonous, superstitious yet charming dandy arrives in Sleepy Hollow, New York, a small village north of Tarrytown and New York City, New York, United States that is renowned for its ghostly hauntings, to be the town's new schoolmaster. Despite his odd behavior and effeminate mannerisms, Ichabod soon wins the hearts of the village's women. Brom Bones, the roughish town hero, does his best to bully Ichabod. However, he is very good at ignoring these taunts and continues to interact with the townspeople. Ichabod then falls in love with Katrina van Tassel, the beautiful daughter and only child of Baltus van Tassel, who is the richest man in the village (unlike in most films, Katrina does not have spoken dialogue in this segment). Despite the fact that he is falling in love with her, Ichabod mainly desires to take her family's money for himself. Brom, who is also in love with her, proceeds to compete with the schoolmaster. Ichabod wins Katrina over at every opportunity, although, unbeknownst to him, Katrina, who thinks Brom is too sure of himself, is only using Ichabod to make Brom jealous and force him to try harder for her affections.
The two love rivals are invited to the van Tassel Halloween party where Brom tries to swap a plump woman for Katrina who is dancing with Ichabod but comically fails. While both men dine, Brom catches Ichabod nervously tossing salt over his shoulder. Discovering Ichabod is superstitious, he decides to sing the tale of the legendary Headless Horseman who was apparently killed by a cannonball in a recent conflict and travels each year on Halloween while searching for a head to replace the one he had lost. Everyone else, including Katrina, finds this amusing while Ichabod, on the other hand, starts to fear for his life.
On his way home from the party, Ichabod becomes paranoid by every animal noise he hears while riding through the dark woods, increasing his fear of the possibility of encountering the Horseman. While traveling through the old cemetery, Ichabod believes he hears the sound of a horse galloping towards him, but discovers the sound is being made by nearby cattails bumping on a log. Relieved, Ichabod begins to laugh with his horse. However, their laughter is cut short by the appearance of the real Headless Horseman riding a black horse (that is, suspiciously, identical to Brom's horse). After the ghost gives chase, Ichabod, remembering Brom's advice, crosses a covered bridge, which stops the ghost's pursuit. However, the horseman throws his flaming skull, revealed to be a great big jack-o'-lantern, at a screaming Ichabod.
The next morning, Ichabod's hat is found at the bridge next to a shattered pumpkin, but Ichabod himself is nowhere to be found. Sometime later, Brom takes Katrina as his bride. Rumors begin to spread that Ichabod is still alive, married to a wealthy widow in a distant county with children who all look like him. However, the people of Sleepy Hollow insist that he was "spirited away" by the Headless Horseman.
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