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The Legend of Sleepy Hollow
Headless Horseman
Title: The Legend of Sleepy Hollow
Directed by: James Algar; Clyde Geronimi; Jack Kinney
Written by: Erdman Penner; Winston Hibler; Joe Rinaldi; Ted Sears; Home Brightman; Harry Reeves
Produced by: Walt Disney
Music by: Oliver Wallace
Cinematography: John Lounsbery; Wolfgang Reitherman; Milt Kahl (Animation directors)
Edited by: John O. Young
Distributed by: Walt Disney Pictures; RKO Radio Pictures
Released: October 5th, 1949
Rating: G
Country: USA
Language: English

"The Legend of Sleepy Hollow" is an animated short produced by Walt Disney Productions in 1949. It was packaged along with another animated short film, The Wind in the Willows on Disney's eleventh full-length animated feature, The Adventures of Ichabod and Mr. Toad, directed by Jame Algar, Clyde Geronimi and Jack Kinney. The film is based on the 1820 short story "The Legend of Sleepy Hollow" by Washington Irving.

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The story of Ichabod Crane and the Headless Horseman, based on Washington Irving's The Legend of Sleepy Hollow (narrated by Bing Crosby). The gangly and lanky Ichabod Crane is the new schoolmaster in Sleepy Hollow. His somewhat odd behavior makes him the ridicule of the rambunctious and robust town bully Brom Bones. Despite his odd appearance, Ichabod quickly proves to be a ladies' man as he charms all the eligible local ladies. Finally, however, Ichabod discovers the local town beauty, Katrina Van Tassel. Katrina is the beautiful young daughter of Baltus Van Tassel, the wealthiest farmer in the area, and Brom's intended. Katrina is a coquette by nature, but sees Ichabod as an opportunity to break from the monotony of Brom scaring away every other potential suitor. Ichabod has his eye on the Van Tassel wealth, and is infatuated by Katrina's beauty and grace as well. After a number of comically unsuccessful efforts by Brom to dispose of Ichabod, the situation changes when Brom decides to take advantage of Ichabod's strong belief in superstitions. Brom musically tells the tale of the Headless Horseman to frighten the teacher. That Halloween night, Crane's lonely ride home becomes exceedingly frightening because of his exposure to the possibility of encountering the ghost. The atmosphere of fear increases in intensity, until it breaks the tension at a false alarm, whereupon Ichabod and his horse laugh hysterically in relief. Immediately, the Headless Horseman appears, laughing maniacally, riding a large black horse that bears a strong resemblance to the one owned by Brom. Then follows a chase scene wherein the Horseman pursues Ichabod with wild abandon, only to be deterred when Ichabod crosses a bridge near the local Dutch graveyard (the bridge being the point beyond which the horseman couldn't go, according to the tale). The Headless Horseman then hurls his own severed head (shown to actually be a fiery jack-o'-lantern), at Ichabod. The jack-o'-lantern bursts into flames as it collides, and everything fades to black. The next morning, the only things found by the bridge are a shattered pumpkin and Ichabod's hat. Brom shortly thereafter marries Katrina. It is later rumored that Ichabod married a rich, plump widow in a distant county, and had many children (all bearing a resemblance to Ichabod). But the people of Sleepy Hollow firmly deny this; they all believe that Ichabod was spirited away on Halloween Night by the ghoulish Headless Horseman.

Later, this portion of the film was separated from the companion Mr. Toad film, screened, aired, marketed, and sold separately as starting in 1958.

The Disney depiction is actually quite true to Irving's original tale, going as far to have some narrative lines taken directly from the text. The important elements of American Romanticism are all included, from the in depth description of the natural, frontierish setting of Tarry-Town, to the description of the brackish hero, Brom, and finally to the element of mystery left to the viewer at the conclusion of the tale.

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