For those of us who live in Tarrytown, New York, a town whose northern neighbor is called Sleepy Hollow, Washington Irving's tale of Ichabod Crane and his encounter with the Headless Horseman is never far from our consciousness. Irving lived here, wrote here and set many of his stories in the area. The image of the Horseman is used in logos for a number of local businesses, and the souvenir shops are chock-a-block with Sleepy Hollow memorabilia, especially since Tim Burton's 'Sleepy Hollow' came out a couple of years ago. The Horseman has decidedly edged out Rip Van Winkle as Irving's best remembered tale, or at least his most heavily commercialized one. The Disney studio produced a terrific Headless Horseman cartoon in the late '40s, by far the best screen adaptation to date, but when it comes to live action the tale doesn't seem to lend itself readily to the cinema, and this silent feature film starring Will Rogers demonstrates why.
The Oklahoma-born Rogers was a most likable screen figure, and on a purely visual level his offbeat casting as Yankee schoolmaster Ichabod Crane works surprisingly well, though he couldn't have played an Easterner convincingly in a talkie. (Although come to think of it, Will did just that in the 1931 version of Twain's Connecticut Yankee; perhaps his casting in that case was something of an inside joke). But anyone expecting a comic rendition of this story featuring Rogers' characteristic wit will be disappointed, for the filmmakers followed Washington Irving's story all too faithfully, giving us an Ichabod Crane who is deeply unsympathetic. We expect comedy when we first see Will dressed as Ichabod, looking so gawky in his 18th century clothes and funny little pigtail, but Rogers plays it straight; his Ichabod is a pompous nerd, just as the story dictates. When the schoolroom sequence begins we expect Our Gang-style gags with pea-shooters or something similar, but this Yankee schoolmaster is self-righteous, prissy and stern. When a boy makes a sassy comment about the local flirt, Ichabod beats him briskly. What humor there is comes from the title cards, generally at Ichabod's expense, as he makes one foolish, arrogant remark after another.
All of this serves the story Washington Irving wrote, but it doesn't serve our nominal star, Will Rogers, or the demands of entertaining cinema. We don't like our "hero" Ichabod Crane very much, in fact he comes off as a jerk: the title cards make it explicitly clear that his courtship of local belle Katrina Van Tassel is driven by greed for her money and property. What a guy! So if we don't like the leading man, who else is there? We are told, again by one of those convenient title cards, that Ichabod's rival Brom Bones isn't such a bad sort, but the next thing we know, Brom is enjoying a cockfight with great enthusiasm -- and shortly afterward, inflamed by jealousy over Katrina, he attempts to use fake evidence to establish that Ichabod is in league with the devil, and nearly gets the guy tarred and feathered by local hotheads. So much for Brom Bones. And as for Katrina, she prefers Brom.
So, we've got a story with absolutely no one to root for, where even the charismatic Will Rogers comes off as a greedy, conceited little schnook, in a town full of rubes, dupes, and superstitious fools. (I should add that where my fellow citizens are concerned, to paraphrase Monty Python, "We got better.") This adaptation of The Headless Horseman does have nice period detail and some amusing touches along the way, and the climactic chase is well-handled and stirring. In sum, however, this film suggests that Irving's Legend of Sleepy Hollow is inherently off-putting material for a live action feature film, and it did so long before Tim Burton proved the point, once and for all.
