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Celebrating 20 Years of Tim Burton’s SLEEPY HOLLOW
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Tim Burton has been the cinematic lord of all things spooky since as early as his first film, Pee-Wee’s Big Adventure, in 1985. Remember Pee-Wee’s nightmarish evil clown dream sequence? He then cemented that reputation over the next decade and a half. He gave us the “Ghost with the Most” in Beetlejuice, and Edward Scissorhands had Vincent Price living in a Gothic castle on the top of a mountain. He then worked with director Henry Selick to bring to life an entire town of Halloween characters in The Nightmare Before Christmas. But it wasn’t until 1999 that Tim Burton finally took all his love of creepy iconography and give us a true balls-to-the-wall horror movie with Sleepy Hollow.

Johnny Depp as Ichabod Crane holding the skull of the Headless Horseman in 1999's Sleepy Hollow

Paramount Pictures

Sleepy Hollow released on November 17, 1999, earning decent reviews and doing solid business. Burton fanatics who loved his creepy aesthetic were thrilled to finally have a true horror film from the director at last. At this point in their careers, Burton teaming up with Johnny Depp, who played Ichabod Crane, was still a treat for audiences. And Burton’s penchant for creating ensemble casts with quirky British character actors together with fresh young faces, like Addams Family’s Christina Ricci, had everyone excited. Twenty years later, Sleepy Hollow isn’t talked about as much as some of Burton’s other movies, but for the most part I think this movie still holds up.

Based on the Washington Irving short story from 1820 — a story embedded into the popular consciousness thanks to the 1949 Walt Disney cartoon — the script was a re-imagining of that story with a much deeper emphasis on the horror of it all. The script was originally developed by makeup effects expert Kevin Yagher and Seven screenwriter Andrew Kevin Walker, before finally catching the attention of Tim Burton. All the right elements came together from a group of people who truly loved the horror genre. And one can see every bit of that love onscreen.

The Headless Horseman rides the countryside looking for his next victim in a scene from Sleepy Hollow

Paramount Pictures

Whatever ambiguity the original classic story had about who and what the Headless Horseman was supposed to be was pretty much tossed out the window with this film. The Horseman (a fantastic over-the-top Christopher Walken) was confirmed to be a mercenary from the time of the Revolutionary War, cursed by witches to become their undead minion. Under their orders, he would chop off the heads of anyone they wished. As the movie’s tagline said, “Heads Will Roll.” And boy, did they.

Played by Darth Maul actor Ray Park in his headless incarnation, the Horseman brutally decapitates some five different people in this movie, including a cherubic little boy! He slices another dude in half just for the heck of it. Despite being a big budget studio film, this movie doesn’t shy away from all the blood and gore. Kids who had grown up with slasher movies in the ’80s who were now adults helped make the film a hit. Some of the convoluted soap opera plotting in this script is indeed a bit of a chore, but when the film delivers on so much else, you pretty much forgive it for its flaws.

The Jack O'Lantern atop a scarecrow in Sleepy Hollow looks straight out of Tim Burton's The Nightmare Before Christmas

Paramount Pictures

In many ways, Sleepy Hollow feels like the movie that Tim Burton was working towards his whole career. He’d always cite his love for the old Gothic-style Hammer horror films from the ’60s as a big influence on his work, and Sleepy Hollow is very much in that vein of those classic frights. It even has a cameo from the king of Hammer horror, Christopher Lee. Those old Hammer films were often overwrought melodramas filled with family secrets and weird conspiracies, something Sleepy Hollow is chock full of. Granted, Sleepy Hollow does it all with a far more self-aware tone than those Hammer movies ever had.

Sleepy Hollow isn’t the best movie in Tim Burton’s career. Not by a long shot really. But it represents “peak Burton” in a way. Up to that point, all of his films ranged from good (Batman, Mars Attacks!) to flat out great (Pee-Wee, Edward Scissorhands, Beetlejuice, Ed Wood). I’d say with 20 years of hindsight, Sleepy Hollow is more on the very good side than the great side, but it gives us so much of the things we loved about Burton’s movies (including a notable musical collaboration with Danny Elfman) before those very same things became cliches.

One of the townsfolk of Sleepy Hollow tries to use his image to scare away Ichabod Crane.

Paramount Pictures

Watching Sleepy Hollow now also is a peek into a career path that Tim Burton ultimately didn’t take. Once the twenty-first century began, Burton largely abandoned his plans to make more horror films. (At one point, he was even discussing a remake of Bride of Frankenstein.) The most notable exception to this being his 2007 adaptation of Sweeney Todd. Aside from that film, most of his more modern oeuvre has been big budget, family-friendly re-imaginings of known IP, like Planet of the Apes, Charlies and the Chocolate Factory, Alice in Wonderland, and most recently, Dumbo.

To be fair to Burton, almost all of these did solid business, so one can see why he went that route. But it was hard to feel the true Tim Burton touch with most of those movies. It wasn’t all a loss these past few years though for fans of Tim Burton’s more personal films, as movies like Big Fish and Big Eyes still had a glimmer of that old Burton magic.

But aside from Sweeney Todd, none of these films can qualify as a horror movie. And this fan of old school Tim Burton would love to see one more stab at the genre from him. Could Burton ever give us a good old fashioned gory horror flick again? Even if he doesn’t, well… at least we got Sleepy Hollow out of him. If you haven’t seen this one in a while, or are a horror lover who has never seen it, we suggest giving Sleepy Hollow a spin this year to celebrate its anniversary.

Featured Image: Paramount Pictures