Why I lose my head for ‘The Legend of Sleepy Hollow’, part 1

I promised you a closer examination of the possibilities that Sleepy Hollow (the FOX tv series) would contain, didn’t I?

Well, you’ll have to sit through a few posts before we get to that, you lucky people. Don’t worry; this one’s fairly short.

Let’s get right down to basics: why do I like the general concept of the Sleepy Hollow mythos so much? Why does the concept of a headless horseman chasing down some poor, unsuspecting schmuck appeal to me so?

Probably because, like a lot of people of my generation (early to mid-twenties, god I feel old) , my first introduction to Washington Irving’s The Legend of Sleepy Hollow was the 1949 Disney musical version, an adaptation that stuck extremely close to its source material.

Capture sleepy hollow 3

For those who may not not be in the know, a quick plot summary – with bullet points!

  • Icahbod Crane, a socially awkward, superstitious, skinny schoolmaster (try saying that three times fast) comes to teach in Tarrytown, which happens to cover the area of Sleepy Hollow.
  • He falls in love with the wealthy and beautiful Katrina van Tassel…
  • …’s father’s money.
  • Katrina herself is in love with Abraham Van Brunt, whose nickname is Brom Bones, don’t ask me why.
  • In order to test Brom’s love, she flirts with Ichabod and invites him to a party at her father’s house, which includes lots of ghost stories.
  • Brom, knowing 1) how superstitious Icahbod is and 2) an opportunity when he sees it, tells the story of his meeting with a headless soldier, who chased him to the brook by the church and then vanished.
  • Ichabod, understandably freaked out by this point, rides home that night – only to find himself chased by a cloaked horseman, whose head does not appear to be attached to his body.
  • A mad chase ensues, and when Ichabod thinks he’s escaped, his pursuer throws the detached head at him.
  • Ichabod pretty much disappears off the face of the earth; Brom Bones marries Katrina and they live happily ever after, while what exactly happened to Ichabod, who the figure who chased him actually was and whether supernatural goings on did occur is entirely up to the reader.
  • (Spoiler: it was probably Brom.)

I loved this film. I still do. It had everything an exuberant child could want: funny looking characters; a hero who was strange looking and who you wouldn’t realise until you were older was a total gold-digger; a ‘villain’ who was actually a pretty nice guy, who we could actually laugh at and who we didn’t really mind ending up with Katrina in the end; a whole lot of slapstick; songs you could really hum; narration and singing by Bing Crosby…

(I was brought up on the Road to… films, okay?)

It also had something that an exuberant child might want, but they’d probably hide behind the sofa while it was on, though still enjoying the heck out of it. Who didn’t watch this film more than once and end up wanting to skip to the last ten minutes, so that we could get a) the best song in the film:

and b) what I still consider to be one of the most frightening chases ever, animated or live action.

I loved loved loved Sleepy Hollow.

Then I read the actual short story when I was about eleven, and my reaction was…


The atmosphere’s good even if Irving’s rather long winded, the characters are interesting and multi-faceted, the chase scene’s nice and scary, but I felt cheated by the ending. This was before I’d come to appreciate ambiguity, so I didn’t like the interpretation that the Horseman was really Brom in disguise, driving Ichabod away with a cruel prank. I also didn’t like that Irving refused to actually just come out and say it.  I’m well aware that was the point of the story, and they did more or less the same in the cartoon. Here’s the thing, though; I’ve always believed that, in the Disney version at least, the Horseman was definitely the real deal, and I will believe it until the day I die.

I mean, look at this.

Capture sleepy hollow 1

That is not a guy in a costume. That is a demon who’s broken free from the bowels of hell and you cannot persuade me otherwise.

Really, I suppose you could say my liking for The Legend of Sleepy Hollow, as a whole, was not because of the main cast, but rather because of a Horseman that might or might not even have existed. Like Schrodinger’s cat, only with more stabbing. And when I was eleven, I really didn’t want an ambiguous, mysterious ending that was left up to the reader. I wanted a real Headless Horseman. What’s more, I wanted him to actually cut some heads off.

On screen.

I was a weird kid. I will not deny it.

Time passed and, a few years later, I discovered that this film existed:

*Haaaaaaaaallelujah, Haaaaaaaaallelujah…*
Awww YES.

…I was a weird teenager. I will not deny that either.

Next time: a look into what makes Sleepy Hollow (1999) so bewildering, barmy, bloody and brilliant.


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