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Will Rogers as Ichabod Crane -- now, that's interesting casting! Opinions were mixed on whether he fit the role or not. While he wasn't quite the physical ideal for the gangling schoolmaster, his gawkiness was certainly in the right place. Sometimes, however, he was too gawky -- when the picture occasionally drags, Rogers seems a bit awkward. The Headless Horseman, of course, is an adaptation of Washington Irving's famed story, The Legend of Sleepy Hollow. When Crane comes to teach in Sleepy Hollow (a Dutch settlement in America circa 1790), he falls for pretty Katrina Van Tassel (Lois Meredith). This does not sit well with Katrina's suitor, Brom Bones (Ben Hendricks, Jr.). First he has Crane accused of practicing witchcraft, but old Van Tassel saves the schoolmaster from being tarred and feathered. Then Brom scares Crane with old ghost stories, and the headless horseman (actually Brom in disguise) chases him out of Sleepy Hollow. In case you're wondering, yes, this picture was a Halloween, 1922 release.