Sleepy HollowReach back deep into your memory. Do you recall The Adventures of Ichabod and Mr.Toad? If at least as old as I am, you'll recall this famous Disney cartoon, made in 1949, which showed every year on one of the local TV stations. Perhaps these may jog your memory:
I don't know for certain when the Headless Horseman became enmeshed with Halloween, but if I had to wager a guess, it is very likely that The Adventures of Ichabod and Mr. Toad is at the center of it.
It was a yearly treat for me and shaped my mind's image the Headless Horseman, the town of Sleepy Hollow and all that's involved in this classic folk tale. After reading the book in grade school, I still had the images instilled from this cartoon hardwired into my brain. It wasn't until 1999 that the wild vision of Tim Burton rewired everything about the way I envisioned Ichabod Crane and the Legend of Sleepy Hollow.
Burton started by making some pretty radical changes to the mythos. Ichabod Crane transformed from a timid school teacher to a squeamish forensic science wielding investigator from New York City, though he still held on to the cowardly, sheepish traits established in the folk tale and portrayed in the '49 cartoon. He confirms on screen that the Horseman is in fact a vengeful ghost, where as it was heavily implied originally that he was a costumed local bully, in competition for the hand of a wealthy land baron's daughter. And Burton also gave Crane a compelling back story, shown in dream sequence flashback, which I won't spoil for you here.
As you could have expected, Sleepy Hollow's setting is heavily Gothic, as is usual with Tim Burton films. It even toes the line with some early, steampunk-esk futurism, mostly with regards to Ichabod Crane's pseudo-forensics. Everything is dark and dreary in this town without hope. The atmosphere is so realized that it can almost be viewed as a character in itself.
The last link that makes Sleepy Hollow so successful is it's ridiculously star studded cast. Just check this out: Johnny Depp, Christina Ricci, Christopher Walken, Christopher Lee, Miranda Richardson, Michael Gough(Alfred!) and even Casper Van Dien (who clearly doesn't want to live forever)! In particular, Walken stands out as the Hessian mercenary turned headless ghost of vengeance.
If you want to watch the very best version of the classic folk tale come alive, check out Sleepy Hollow. It totally couldn't hurt to check out The Adventures of Ichabod and Mr. Toad as well, for old times' sake.