“The Legend of Sleepy Hollow” is one of the classic American horror stories, and for good reasons. It has a wonderful monster and one of the scariest chase scenes in the written word. It is also, at times, very funny. All of that said, I find the original short story, well, problematic.
Washington Irving’s story is viciously anti-intellectual. There is no way around it. Ichabod Crane, the protagonist of the story, is presented as being ugly, stupid, greedy, amoral, pathetic, and as unsympathetic as you can make him without actually having him, like, murder people. You are not supposed to like Ichabod Crane – you’re supposed to laugh at him and be slightly repulsed. He is a loser, and not the likable kind. And he is a loser because he is an intellectual. The narrative links all of his character flaws to the fact that he prioritizes book learning over doing manual labor. Haha, what a stupid chump this guy is for knowing more than basic addition and subtraction! Hohoho, how pathetic is this loser who probably knows something about other cultures? I bet he even reads books for fun!
Ichabod’s role as a teacher is particularly mocked in the story. The U.S.A. didn’t have mandatory public education when “The Legend of Sleepy Hollow” was published, and the idea that anyone other than rich kids would go to school was considered laughably stupid. How the hell is learning how to read going to help you work on the farm? So the traveling teachers who would go around at the time trying to educate all these rural kids were treated like dirt, with many being forced to live basically like hobos begging for scraps. All because they thought there was value in helping everyone get smarter. Ichabod Crane is basically every bad stereotype about teachers you can think of rolled into one character – he’s petty, smug, shows explicit favoritism towards students with well off families, hands out punishments without rhyme or reason, and, worst of all, is actually incredibly stupid despite trying to “teach” others. He is basically anti-teacher propaganda.
Then you get Brom Bones, the manliest of manly men, who works big manly jobs that involve lifting heavy things and shows off his manly physique and isn’t so keen on this book learning nonsense. You are supposed to love Brom Bones. Brom Bones is what a man should be. He’s so damn manly and strong and big! And he has trouble expressing his emotions and commiting to the woman he loves because he’d rather be a freewheeling bachelor and do manly things but he also doesn’t want anyone touching his girl! Brom Bones is basically Gaston from Beauty and the Beast, except you’re expected to root for him. And we’re supposed to cheer when he teases and mocks ugly, pretentious, and effeminately emotional Ichabod Crane.
I’d like to think our values have changed a great deal since this story was published, as I think many people reading the story nowadays would have trouble hating Ichabod as much as Irving wants us to and liking Brom as much as we’re supposed to. I’m offended by it for personal reasons.
There’s also the pacing of the story. The first 4/5 of “The Legend of Sleepy Hollow” aren’t really a horror story. They’re more of a farce about how stupid and ugly teachers are and how hilarious small town shenanigans are. It’s kind of dull and grating. So why the hell am I including this story in my series?
Because that last fifth is BADASS AS HELL.
If you can stomach all the nerd-hating dudebro horseshit at the start of the story, you will be rewarded with one of the most gripping ghost encounters in American fiction. The writing of that big end chase scene is so so so so so so SOOOOOOOOOOOOO good! The Headless Horseman takes the last few pages of the story and makes everything – EVERYTHING – worthwhile. He’s just a wonderfully compelling villain – an unstoppable cackling force of death whose very presence turns a forest into the spookiest haunted woods you could ever hope for. It is worth it. It is so worth it.
That chase scene, of course, is the one thing most people actually remember about the story. Most forget the rest of the crap, either because they were too bored to pay attention or because they’re trying to force it out of their memory (like me). This is why I actually prefer the adaptations of “The Legend of Sleepy Hollow” to the actual story: they tend to take that last chase scene and spin a whole new story out of it, one where intellectual Ichabod is presented as much more likable. I’m not going to say I like ALL adaptations of the story, because I haven’t seen them all, but I will talk about the three I’ve seen and enjoyed.
The most faithful, and thus the most grating, is the Disney short. Disney is actually very true to the story for the most part. Sure, they pruned the stupid small town shenanigans aspect down a bit – it is now only 2/3 or so of the plot instead of 4/5, but they still follow the general plot to a T: Ichabod comes to town, gets picked on by macho man Brom Bones, tries to steal Brom’s sexy girlfriend, prank off ensues, Brom tells the horseman story, Ichabod is chased off by a spectral horseman, ambiguous ending where Brom gets the girl and Ichabod either left town or got straight up murdered. Pretty much the same. The Disney cartoon is nicer to Ichabod, though, presenting him as a likable goof instead of a despicable schmuck. They still present Brom Bones as a good guy though, so, y’know, marks off for that. Like the story, it’s really best if you just skip to the ghost story section and go from there. The Headless Horseman song is a gem, and the chase afterwards is one of the most thrilling, Halloween-tastic moments of animation in history.
Then there’s the Tim Burton adaptation, Sleepy Hollow, which is by far my favorite take on the story. Burton jettisoned the bulk of the plot and basically made Sherlock Holmes vs. the Headless Horseman, and that’s fantastic. Well, it’s actually more like Effeminate OCD Scaredy Cat Sherlock Holmes vs. the Headless Horseman, but that makes it even better. The Burton version takes the traits Irving was mocking – analytic reasoning, education, rational thought, being in touch with your emotions, valuing brains over brawn, etc. – and makes them heroic. His Ichabod Crane is a champion of intelligence and reason, trying to convince people to change their ways and adapt so they can do away with the superstitions and prejudices of the past. It is a complete turnaround of the themes of the story, and I approve that wholeheartedly. The movie is also a loving homage to the Universal and Hammer horror films of the past, which I love as well.
Last is a show that just came out which also goes by the name Sleepy Hollow. It goes even farther than the other two, with Ichabod Crane unknowingly traveling in time to the present day (a nice reference to another Washington Irving story, “Rip Van Winkle”) after fighting the Horseman off in the Revolutionary War. He then teams up with a detective to stop the Horseman from causing the apocalypse by raising witches, demons, and other monsters of the week. It’s very formulaic and has very little to do with the original story, but the writing is good so far and it’s a fun show to watch. It doesn’t make me literally angry with rage like the first 4/5 of the original story, so that’s a plus too.
The Headless Horseman himself is a timeless monster. Washington Irving didn’t invent the character, as the horseman was actually taken from a German folktale, and similar ghosts and monsters exist in other myths all over the world. Irving’s take is the iconic one, however, and I imagine many people have been inspired by some form of “The Legend of Sleepy Hollow” when they don their huge-shouldered capes for Halloween and pretend to be a headless ghoul. Here’s to you, Headless Horseman. You’re the only good thing in that fucking story.