
Sleepy Hollow (1999)
Director(s): Tim Burton
Writer(s): Washington Irving, Kevin Yagher, Andrew Kevin Walker
Starring: Johnny Depp, Christina Ricci, Miranda Richardson
My first foray in the mythos of the headless horseman was surprisingly around the second or third grade. It was one of those rainy days, where playing outside during lunch break was not an option so the next best thing to satiate us little demons was to put on a movie. On this day, our teacher popped in a VHP tape of The Legend of Sleepy Hollow (you young pups can look up what a VHS tape is on the interweb). This animated short told the tale of Ichabod Crane and how he gets entangled with the legend of the Headless Horseman; a terrifying headless spirit who rides their horse through Sleepy Hollow terrorizing the locals. At this point, my horror muscles were certainly being developed so something like a spooky short didn’t really phase me, but I did find the plot quite interesting and by interesting, I mean super frustrating!!! Without spoiling anything, the short ends with a question mark without much resolution and then the credits basically roll with cheery music in the background when the final fate of the main character was never confirmed (they did state some rumors of what happened afterwards, but still not satisfying). For a kid who constantly expected closure, the ending was such a letdown, especially after enjoying the visuals of the Headless Horseman throughout the short.

Cut to 1999 and at this point I was a full-fledged horror geek, and I was delighted to find out that none other than Tim Burton was going to give his take on the Headless Horseman. I already figured what the look and tone was going to be for this flick, since his macabre, goth style was the perfect backdrop for this kind of tale, but I must admit, I was concerned that Mr. Burton was a huge fan of the Disney short and may go the same direction with THAT ending but within the first couple minutes of the movie, I was definitely convinced that this was Tim Burton’s vision of the story. The feel of the movie definitely has its roots in horror but comes off more like a murder mystery where the Headless Horseman is more like a tool for violence and part of a bigger picture rather than the main focal point, so the audience is free to try to figure out who is really pulling the strings. The plot itself has you guessing since they introduce a barrage of characters, all with personality quirks and perceived motives so it really plays out like a good mystery intertwined with the thrills and gore you can expect from a Headless Horseman.


A smart move to move the plot in the right direction was having Ichabod Crane be a constable who is investigating a string of murders at Sleepy Hollow rather than an unsuspecting schoolteacher. However, what I loved about Johnny Depp’s performance was that he kept the spirit of the character who is a skeptic of anything paranormal in a brainy, sort of adorably geeky way which makes Crane a very likeable character to the point where you end up rooting for him to solve the mystery and (hopefully) escape the clutches of the horseman. Christina Ricci (fun factoid; my first celebrity crush when I was in elementary school after watching The Addams family) does a great job in the flick being the counterpoint to Crane since she is definitely more of a believer of the occult and the spirits which undoubtedly makes her a prime suspect as well.


Besides the fantasy, gothic vibe that is synonymous with Tim Burton, the horror factor is quite strong in this flick that is reflected through it’s kills and overall gore. I love the look of the Headless Horseman in this flick and his attire is directly correlated to his backstory which is another thing I love about this flick since you might as well give an origin story to a legendary horror figure to fill some time since this was a full-length flick as opposed to a short. This movie was very clever on how to expand the mythology of the Headless Horseman in a way that makes sense to drive a plot forward. The way the character was utilized by making his origin a key part of the story (trying to stay spoiler free here folks) was a great move because the payoff on the “who dunnit” part of the story is quite satisfying and the consequence of using the Headless Horseman is even MORE satisfying. Overall, this movie was almost cathartic for me on how it gave me closure on Ichabod Crane and gave me some great background to the Headless Horseman himself so young elementary school me was thanking Tim Burton.

Not going to spoil who plays the Headless Horseman but let’s just say he’s always yearning for a sound, a clanging sound that is directly associated with one of the most iconic farm animals…
Life is FAR more interesting when we take interest in things that scare us.