Long before Johnny Depp or Bing Crosby's voice, the inept schoolmaster of Washington Irving's classic American novel The Legend of Sleepy Hollow was first played by cowboy funnyman Will Rogers in 1922. Rogers was still relatively new to film at the time, but not to entertainment. He was already the toast of Vaudeville for his trick roping and incisive political wit. In 1918 he was signed by Samuel Goldwyn and moved from New York to Hollywood. It was there that he starred in The Headless Horseman.
Aside from being the first screen adaptation of the Irving story, The Headless Horseman may also perhaps be the silver screen's first horror-comedy. Unfortunately, Will Rogers' comedy was based in the powers of speech, which is a detriment when it comes to silent films. A humble, "aw shucks" demeanour gives it a go with the limited silent-era slapstick, but this trick roper's hands are tied in this medium.
However, one doesn't watch a flick like The Headless Horseman for laughs. The story is, like the novel, primarily about the love triangle between Ichabod Crane, Katrina VanTassel, and Brom Bones. But when the title character rears his decapitated shoulders, the limitations of silent film become tried and true assets. A simple double-exposure was all that was needed to create a scene more bone-chilling than anything Tim Burton's computers could muster.
Nevertheless, any film adaptation of the Legend of Sleepy Hollow must compare with Disney's near-monopoly on it, even if it was made before Bing crooned the audience. Disney's version still benefits from it's short length, providing a tighter story that doesn't waste time getting to the part everyone wants to see. It has another advantage over the 1922 film: part of the fun is the ambiguity over what the Horseman is... Is is a ghost? Or was it Brom Bones? Was Ichabod spirited away, or was he alive and well in New York? Disney never tells. However, this version of the film does, losing some of the mystique in the process.
There is a way to regain some of it though. Save The Headless Horseman for just the right moment... A dreary autumn afternoon in October, dried leaves rustling in the wind, the ever so faint laughter of children being carried on the wind, the hooting of owls and cawing of crows, the smell of decay, the dwindling sunlight, the harvest, the feeling of Halloween... Just the kind of dusk described by Coleridge...
Like one, that on a lonesome road
Doth walk in fear and dread,
And having once turned round walks on,
And turns no more his head;
Because he knows, a frightful fiend
Doth close behind him tread.