Headless Horseman Halloween Oblivion

I don’t know about y’all, but when late October comes around it means it’s time to curl up with warm apple cider (mixed with Goldschläger) and watch old Halloween specials. My repertoire of favorites includes the obvious It’s the Great Pumpkin Charlie Brown, as well as Ray Bradbury’s brilliant The Halloween Tree, sometimes Hocus Pocus, Halloween (Carpenter or Zombie), Trick ‘r Treat (very underrated) Halloweenie (Pete & Pete), Tricks and Treats (Freaks & Geeks) Pink Eye, Spookyfish, Korn’s Groovy Pirate Ghost Mystery (South Park) any of the Treehouse of Horrors (Simpsons) or even Disney’s Halloweentown. But this year, on top of some of these classics, I’ve been harping on another old Samhain memory; the rarely shown Disney cartoon of The Legend of Sleepy Hollow:

I remember watching this many years ago, a cold October night, terrified. It’s pretty scary for a kids cartoon, the ending implies that Ichabod was killed or otherwise spiritually burglarized by the Horseman, a rather dark interpretation of the story.

You see, the original Legend of Sleepy Hollow by Washington Iriving wasn’t so clear cut. Being written word and not visual storytelling, the identity of the Headless Horseman was more shrouded in mystery. Maybe it was a ghost, or maybe it was just Brom Bones trying to scare away his sexual competitor. It was up to the reader to decide. Here Disney gives us a ghost, and a scary one at that, which I guess we could interpret as just a manifestation of Ichabod’s mind, but as a kid you don’t get that far, you stop at “that’s a freaking ghost,” and then you have nightmares for weeks.

Upon further inspection I realized that the story gets retold lots of different ways. Some go for the dark and gory, some for the humorous, some for a blend. Sometimes Ichabod is an imbecile, sometimes a genius, sometimes superstitious, sometimes skeptical. The Legend of Sleepy Hollow is one of the oldest American ghost stories ever written, so media has had it’s way with the tale many times over. I’ve been losing myself in the mad plethora of ways this classic’s been done.

So grab that cider and chill back, here’s more headlessness than you’ll ever need.

First off, here’s the full version of the Disney cartoon as it originally appeared, complete with a fascinating animated history of Washington Irving (and the real Sleepy Hollow) as prologue.

As the prologue demonstrated, the legend of the Headless Horseman was popular in oral folklore long before Irving wrote it down. His narrative is simply the way that many different stories from all over the northern New York region were condensed into a single written piece, much the way that certain New Jersey  variations of the “Cropsey” legends were condensed into The Burning.

I’ve always liked Disney’s interpretation, the song’s are great, the ghost is terrifying, but they really chose to do Ichabod as kind of a dick. I mean, sure he’s a ladies man, he’s the only guy in town who can out woo Brom Bones, which gives him some G status, but he’s also conniving, oppurtunistic, and manipulative. As we see, he uses his position as “pedagogue” (a strangely specific term to use repeatedly) to lord over the classroom and basically get fed every night of the week. First he uses women for their cooking abilities, and then, when Katrina comes along, we see a whole new form of opportunism. Sure he’s probably sexually attracted to her, assisted by the aphrodisiacal prospect of her “dowry.” Can he even tell the difference between her and the land she comes with?

“Katrina, my love, who can resist your grace, your charm…and who can resist your father’s farm!”


Maybe it’s so kids won’t feel too bad when he gets decapped and the stereotypical jock gets the girl instead. I sure didn’t mind.

Though the most culturally prominent, Disney’s cartoon isn’t the only, nor even the first, animation of Irving’s Legend. In 1934 ComiColor had produced their own Headless Horseman, choosing to go for a far more humorous, lighthearted interpretation of Ichabod’s ride.

Yes, this cartoon certainly is racist (as was unfortunately typical of animation of this era) and maybe even a little homophobic (Brom was ready to kill Ichabod over that accidental kiss) but it still makes me laugh. 30’s cartoons are just so ridiculous. I don’t know what those animators were smoking.

Also it’s interesting that they chose to interpret the story as a completely natural (as in not supernatural) chain of events between two men, no real ghost involved, just people sabotaged by their own superstition.

But before even this the story had made it’s way to the screen. The Headless Horseman (1922) went the same route Disney would later go, as in Ichabod as an asshole, and the Horseman as an indisputably real ghost. The New York Times wrote at the time of it’s premier:

“The only thing distinctly cinematographic about the film is the acting of Will Rogers. He is in truth Ichabod Crane come to life. It is a positive pleasure to watch him. The scenes of Ichabod’s ride, too, when he is pursued by the headless horseman, are also well done. They are excellently photographed and effectively composed.” (The Screen, New York Times Dec. 25 1922; p. 23, Ichabod Himself)

Silent films get a bad rep these days, mostly because (let’s be honest) by modern cinematic standards, they’re boring. But try to think of pictures the way that people in 1922 did, not so much as something that requires our rapt attention (as with talkies) but rather an interplay of images over which one can talk, laugh, scream etc. Picture houses were a place to gather and chill, people would come in the middle of a movie and stay until two thirds through the next one. Get a couple friends together, roast some pumpkin seeds, and put this on as visual entertainment. Feel free to talk as much as you want, the actors have nothing to say.

Moving on now I must ask the question, is there ever a part Jeff Goldblum was more suited to play than Ichabod Crane? Arrogant, eloquent, dandy, sophisticated, and flirtatious. I could be describing either one of them. Well, the match made in heaven came to be in 1988 with this modest but admirable T.V. adaptation of the Legend.

But T.V was just getting started with Sleepy Hollow. Crane and the Horseman are so deeply ingrained in American storytelling culture that the legend (and it’s many variations) continued to appear in multiple television shows.

Firstly, it got yet another straightforward retelling in Shelly Duvall’s Tall Tales & Legends.

Then it got a “hip” modernization in the cult animated series The Real Ghostbusters (fans of Ghostbusters will either love or hate this show) with “The Headless Motorcyclist.”

And how could such a classic ghost story pass without getting a treatment from our neighbors to the north, the Midnight Society. This is actually a landmark episode of Are You Afraid of the Dark as it marks the departure of Kristen and David and Tucker’s entry into the society. That’s a good or a bad thing depending on how you feel about Tucker, personally I thought he was cool right up until the New Midnight Society.

I love how the two kids at the end just totally sell Ichabod out. They’re like “peace dude, better you than us.” I think it’s a testament that Ichabod’s always gonna be running from the Horseman, people are never going to get sick of creating his midnight Halloween ride.

And so, still not allowed rest, Irving’s Legend, had the honor of being related by the most literary Jack Russel Terrier to ever grace the airwaves. I must say, Wishbone gave me my foundational literary knowledge far before I could read independently, but he also scared the hell out of me time and time again. I remember many a sleepless night, be it after the Faust episode, Wishbone’s retelling of Frankenstein, Rip Van Winkle (also by Irving), or The Phantom of the Opera. This episode was up there as well (still Faust was probably the most traumatizing. I was raised Christian.)

Like Are You Afraid of the Dark, Wishbone always managed to draw a clever parallel between the story and the storyteller (or general framing.)

(Note: Unfortunately this episode starts 9 minutes in. You can probably piece together the plot pretty easily [or from memory if you watched this as a kid] but rest assured that I will update this link as soon as part 1 is reuploaded.)

Sometime after all this, there was yet another TV movie adaptation in 1999, though I don’t see how Brent Carver could possibly outdo Jeff Goldblum’s Ichabod (though who am I to talk, I haven’t seen this one, can’t find it anywhere.)


Until we finally arrive at the most recognized feature film adaptation of the legend (I must say, Tim Burton really monopolizes the classics, not always for the best, everything gets the Burton drab wash and semi-comedic over-the-top gore, though I think in this instance it worked well) starring Johnny Depp as Crane, this time a policeman not a schoolteacher, and skeptical rather than superstitious.

I watched this movie for the first time with my mother around Halloween when I was in 5th grade. She agreed to rent it because of the period dress (this is the same reason she took me to see From Hell) not knowing that I was totally tricking her into renting a horror movie (not strictly allowed back then.) In the proceeding two hours, she realized her mistake and insisted that I cover my eyes several times (which I only pretended to do, the same as with From Hell.) Personally I enjoyed Depp’s Crane, I think it’s the most likable depiction of him yet, and Ricci’s Katrina is clever and sexy, but I do think that Burton over-complicated what was already a satisfactory story. We don’t need all that extraneous mystery solving, honestly I was happier with the simplicity of one midnight ride, one Halloween night.

Less refined but good campy fun is The Hollow, a 2004 ABC Family Channel movie about a descendant of Ichabod Crane who must, with the help of his sassy blonde girlfriend and the town bully (who’s soft on the inside), stop the Headless Horseman’s ghost (we’ve seen even this retelling retold a couple times i.e. AYAOTD Midnight Ride, and there’s another elusive kids special produced last year called Halloween in Sleepy Hollow with the Crane descendant aspect)

I think this is actually one of Kaley Cuoco’s better performances (fie on thee for ruining Charmed, but we’ll get to that in a sec, yeah but unlike Charmed she’s not unbearable in this)

Recently there’s been another modern, horror adaptation. I haven’t seen it and the trailer fails to entice me:

Oh god. They did it. They made the most obvious joke in the world, connecting oral sex to the headless horseman. That line’s been staring every writer to ever reinterpret Irving’s Legend in the face since he wrote it, but no one’s been classless enough to do it…until now.

I mean the joke writes itself. Think about it, Ichabod goes home headless and gets headless. He doesn’t get any Katrina, and gets headless. Get it? I can say it a couple more times if you don’t.

Besides, Lupe Fiasco already owned this joke, he did it the only way it could possibly be done with any finesse i.e. as a rap lyric.

“Now I’m brainless, which means I’m headless

Like Ichabod Crane is, or foreplayless sex is”

From Dumb it Down off Lupe Fiasco’s The Cool

Very clever. I think that’s the one time this joke needs to be made, check it off the list.

Moving on:

I was once a big Charmed fan, mainly because I had seen principally 3rd and 4th season reruns on FX not realizing that I was seeing only the show’s creative crescendo and never the mediocre flanking (or abysmal conclusion.) 1st and 2nd season were cute and enjoyable, 3rd and 4th season are gold, from there on it’s hit or miss, probably at a ratio of 2 misses to 1 hit in Season 5, up to 4 misses to a hit in Season 6, and persisting at said ratio through Season 7 until Season 8 when it’s almost all misses.

That said, this Irving inspired Season 6 episode is alright. If I had to call it I’d say it’s a hit. You have to be in a very particular mood to get into Charmed, but if you’re there it can be good fun.

What will be next? Ichabod can’t rest for long. Soon someone will resurrect his terrified ride, someone will cast the ghostly Hessian soldier back behind him, someone will tell the legend yet again. Not to mention, there are probably at least a hundred more adaptations that I don’t know about:

I’ve been thinking about the Horseman a lot when I’m biking around at night. Sometimes I feel his decapitated specter clopping up behind me, ready with the sword. Other times, when I am riding fast, my bike light flashing through the October night, I assume the dark aspect and I become the Horseman. I guess that’s what Halloween’s all about.


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