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By Dan Brooks

It was always there, waiting to come out. Throughout Tim Burton’s ’80s and ’90s rise, he mostly told stories about misfits and outcasts (Beetlejuice, Batman, Edward Scissorhands, the list goes on), with some moments of fright (looking at you, Pee-wee’s Big Adventure’s shape-shifting Large Marge, who scarred me for life). He displayed a distinctive visual style, one that often focused on gothic and dark imagery, recalling the atmospheric Universal Monsters films. Burton has also acknowledged a great appreciation for the UK’s Hammer horror films, watching them religiously in his youth. “My parents told me that I used to watch horror movies before I could walk or talk,” the director told the American Film Institute. “The odd thing was, I was never afraid of them. I gravitated toward monsters and monster films.” Clearly, this was a filmmaker who loved things creepy and weird, but he had never made an actual horror feature. That is, until 1999’s Sleepy Hollow.

Coming off 1996’s Mars Attacks!, Burton chose an adaptation of Washington Irving’s classic 1820 short story, “The Legend of Sleepy Hollow,” as his next project. “The only literary works I’d brought to the screen were comic books,” Burton told The New York Times upon release. “I’d known the ‘Sleepy Hollow’ story from school and from the Disney cartoon. It had an interesting mix of humor and spookiness, action and design, which I liked.”

It was, in retrospect, kind of a perfect match. “The Legend of Sleepy Hollow” centers on Ichabod Crane, a schoolteacher working near the supposedly haunted village of Sleepy Hollow, New York. Ichabod is awkward and skittish, not unlike Burton’s usual oddballs. The local legend of the Headless Horseman tells of a spectral soldier who looks to recover his head while claiming victims. He’d be right at home in Beetlejuice. Even the setting makes sense for the director, who just six years prior had dreamed up The Nightmare Before Christmas. To wit, Sleepy Hollow, as described in the short story: “The whole neighborhood abounds with local tales, haunted spots, and twilight superstitions; stars shoot and meteors glare oftener across the valley than in any other part of the country, and the nightmare, with her whole ninefold, seems to make it the favorite scene of her gambols.” What’s more Tim Burton than that?

In “The Legend of Sleepy Hollow,” Ichabod plots to marry Katrina Van Tessel, daughter of a wealthy farmer and land owner, in order to inherit her family’s property. She rejects him, however, and Crane encounters the Headless Horseman shortly thereafter. His ultimate fate is left ambiguous, though it’s insinuated that the specter was just a disguised Brom Van Brunt — Ichabod’s rival for the affection of Katrina. Burton’s film, from a script by Andrew Kevin Walker, would go deeper and scarier than its source material. 

For Sleepy Hollow, Burton cast Johnny Depp as Ichabod, reuniting with his Edward Scissorhands star. This Ichabod, more noble than the Crane of “Legend,” is a constable sent to Sleepy Hollow to investigate a series of beheadings. A city man of science and reason, Ichabod is decidedly out of place in this superstitious town that’s more a relic of the old world. A classic Burton outsider. Christina Ricci’s Katrina plays a larger role than in the original tale; she’s sharp, interested in witchcraft and a companion to Ichabod, as well as a love interest. The Headless Horseman looms over the film, and it doesn’t shy away from his evil deeds, though there’s also a tragic element to this villain — after all, Burton loves his monsters too. There are several important new characters, as well as schemes, conspiracies and mysteries that Ichabod must solve. Sleepy Hollow is based on the short story the way Burton’s Batman is based on the comics, which is to say, he took a few strands of its DNA and created something new.

Though Sleepy Hollow was a hit, grossing $207 million worldwide, it feels somewhat forgotten among Burton’s bigger triumphs. And that’s unfortunate, because it’s a great mix of humor and horror in the tradition of its director, and the film presents some intriguing themes. It actually reminds me of Ghostbusters, as Sleepy Hollow pits science against the supernatural, and Ichabod must open his mind to the paranormal. There’s also the idea of the city versus the rural. I find all this especially interesting against the backdrop of 1799, the year in which the movie takes place: The country was new, the Industrial Revolution had arrived, and the possibilities of technology were just dawning. But the old ways remained. That’s a rich setting for a ghost story.

There’s also, significantly, the horror of it all. Sleepy Hollow received an R rating and deserved it, as Burton goes hard into violence and gory imagery. “Heads Will Roll” was the movie’s tagline, and indeed they do. We also see the leftovers of his attacks, and it ain’t pretty. But there’s an intensity to Sleepy Hollow that felt new for Burton, particularly one sequence where the Headless Horseman stalks and shows no mercy for his targets, and it’s shocking. 

Sleepy Hollow is also very funny in places, with Ichabod performing autopsies one moment, cowering under blankets the next. Not quite an action hero, but then, the movie would be less interesting if he were.

Sleepy Hollow came at a time of evolution in effects. (Star Wars: The Phantom Menace, a watershed moment in digital imagery, arrived just six months prior.) It’s a gorgeous movie, with real sets, practical effects and select use of CG. “Having completed the fun and zany sci-fi work from Tim Burton’s Mars Attacks! just a few years prior, I was heralded into his dark and funny depiction of ‘The Legend of Sleepy Hollow,’ ” Industrial Light & Magic’s Robert Weaver, computer graphics sequence supervisor on Sleepy Hollow, tells me over email. “While humor always dances around his projects, Tim wanted to have the Headless Horseman dramatically dark and real. The creative decisions led to the interesting work that ran the gamut from environment extensions, removal of said horseman’s head, to graphically real decapitations that paved the way for the evolution of fluid simulations. I was one of many kids in the candy store savoring the ability to bring these moments to life.” (Weaver will be the guest for a virtual talkback following IPH’s screening of Sleepy Hollow on Oct. 29.) In some ways, Sleepy Hollow looks and feels closer to modern fare that seeks a balance of practical and digital effects than it does to other films of its era.

Now 25 years old, Sleepy Hollow has aged well. Maybe that’s because it is Burton truly embracing his horror roots, going back to what inspired him to make movies (see the Christopher Lee cameo, a tribute to his Hammer films Dracula hero), while still playing to his other strengths in romance, thrills and design. This Halloween season, I can think of nothing better to recommend.

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Dan Brooks is a writer who loves movies, comics, video games and sports. A member of the Lucasfilm Online team for over a decade, Dan served as senior editor of StarWars.com and Lucasfilm.com and is the co-author of DK Publishing’s Star Wars Encyclopedia, coming in November. Follow him on Instagram and X.
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