The first full-length attempt to turn The Legend of Sleepy Hollow into a movie was often said to be a failure in that nobody could imagine Will Rogers as a northern schoolmaster. It's worth noting that, when this came out, Will Rogers was one of the biggest stars in the country, and was considered an American icon. Everyone knew his act, and everyone at least had a general idea of what he sounded like. The guy made 71 movies before 1935!
These days, it's not so hard to imagine him as Ichabod Crane, since most of us really DON'T know what he sounded like, or, if we did, we can imagine him outisde of his usual shtick. He's as good an Ichabod as any other live action version, despite the general lack of lankiness. He doesn't look the part, but he plays it pretty well.
There are some REALLY cool scenes here - there's an early one showing a a ghostly form with a skeleton hand leading a horse through a churchyard as Crane is told the story of the headless horseman. It's not as spooky as, say, a German Expressionist horror film (man, would I have loved to see those guys take a crack at this story), but it's spooky by the standards of the day. Then there's the scene were Ichabod walks among the graves between services at church, entertaining the ladies by making up funny epitaphs, which isn't really in the book, but would have fit right in.
Ichabod is portrayed as hilariously vain and full of himself, shocked when the local yokels show a lack of respect for an educated man. All versions have to mess with the character of Crane to stretch the story out, and this one plays up his vanity. Other than that, it stays remarkably true to the original, leaving very little out. To this day, I don't think a single other version has used so many scenes and gags from the original story. Why, they even call the party a "quilting frolic," and the horseman actually turns out to be Bones, not a real horseman (the only movie to do either, really). After a while, though, it veers into new territory - Ichabod is accused of witchcraft, and narrowly avoids being tarred and feathered (a process which was MUCH more painful and deadly than we generally think of it as being today*), which is a pretty interesting way to fill time.
Of course, it suffers from some limitations - most of the movie isn't all that visually exciting, given the subject matter. And it spends WAY too much time showing dull shots of people talking -which are all the more dull, since you have to wait until the title card comes up to see what they're saying. If you're a reasonably fast reader, you can probably do fine watching it on fast forward most of the way through.
Still, this version stays truest of all versions to the original, and probably does the best job of coming up with new material to fill time for the story.
* - for more information about tarring, feathering, and the late 18th century, see The Smart Aleck's Guide to American History!
Here's a 51 minute version - about 20 minutes shorter than the one that goes around on DVD, and with a jazzy score that starts out sounding cool, then gets a bit irritating after a while. The time difference MIGHT just be due to speeding it up or something. That happens sometimes with these silent things.
And here's another version that clocks in at 70 minutes. The organ gets a bit old after a while.