By Kyle G. King. This is RETROGRADING, where it is you, Ichabod Crane, who is now put to the test.

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THE FILM: Sleepy Hollow

THE TIME: 1999, when Tim Burton and Johnny Depp’s relationship was still only at third base. Though they fell in love on Edward Scissorhands and maybe kissed a little during Ed Wood, Sleepy Hollow helped them discover their shared kink of period pieces and wearing long black coats.

RECOLLECTIONS: The summer of ‘99 was a treasure trove of blockbuster releases. Austin Powers, The Mummy, and American Pie all began their franchises that season. (Even Star Wars got back into the swing of things.) But it wasn’t until November that Paramount would release Tim Burton’s first bonafide horror feature in Sleepy Hollow, on a weekend where the film would be pitted against Toy Story 2 and Bond flick Tomorrow Never Dies (both of which severely lacked in gruesome decapitations). Part detective caper, part vengeful ghost-tale, Sleepy Hollow was a ret-conned literary classic that took the pompous fun of British theater acting to the dreary and gothic woodlands of folk tale horror.

In 1999’s autumnal landscape, Sleepy Hollow blossomed, riding the #2 spot just behind James Bond on its opening weekend. Though reviews were only warm, not quite hot, the carnival attraction of a headless horseman chasing meek, beautiful, Johnny Depp was just fun enough for critics and audiences alike. Depp proved once again he was anything but a typical leading man, and Burton put forth further proof that fear and comedy can compliment each other gracefully.

Nominated for three Oscars (winning one for best art direction), Sleepy Hollow did great things for all involved (it pushed cinematographer Emmanuel Lubezki forward with his second Oscar nomination). And yet, somehow, Sleepy Hollow has been nearly written out of public awareness, as all of its players went on to create bigger and bolder (not necessarily better) things.

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THE DIRECTOR: When we’re told scary stories, generally before bedtime from an older sibling or in a group around a campfire, the visuals in our head loom large. Buildings tower over people, shadows drag on into infinity, lightning strikes with portentous doom, and the characters that populate these tales are altogether extravagant — either timid and helpless or brooding and powerful. As kids (or adults with beards who scare like kids) our imaginations love to explore the space within a well-told story, our fear the only thing that keeps us from going too far.

But Tim Burton, a goth kid all grown up (theoretically), has never been very interested in restricting his imagination or constraining his own phobias. Burton is and has always been focused on pushing the normal into the weird, the fearful into the playful. Sleepy Hollow brought all the visuals we make in our heads to life, as Burton held the flashlight under his face menacingly.

Though he had already made his way as a cinematic journeyman, the niche middle ground of fun fantasy and goth action finally began to synthesize with Sleepy Hollow. While the bloodshed might have been bigger in Burton’s 2007 movie-musical, Sweeney Todd, Hollow remains Burton’s most viciously gory. Eighteen heads pop off altogether, in a tale that strays playfully from the Washington Irving original.

Burton was more interested in his own odyssey than that of Ichabod Crane’s (now a city detective instead of Irving’s school teacher) and it shows — the sleuth aspect of the script’s whodunit pales to the film’s much grander visuals. As the master and his man-muse moved forward towards an uncertain artistic future, Sleepy Hollow remains one of Burton and Depp’s more fascinating (and angsty) experiments.

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THE CAST: Four years before Pirates of the Caribbean, Johnny Depp was still known for more modest roles. Playing neurotic, clinical, and cowardly Ichabod Crane gave him an opportunity to let the world see the particular shape of his dynamic freak flag. Initially as a non-believer to the ghostly, Depp has contagious fun as he transitions Crane from a man of science to a man that does battle with a paranormal headless swordsman. The sparkle in Depp’s eye is still bright, compared to what we’ve seen in his other more out-there roles that followed.

Just as Sleepy Hollow was Depp’s opportunity to bring his oddball shtick to the mainstream, Christina Ricci used it to announce she’s not child actor anymore. Though, she had been simmering under the radar with indies like Vincent Gallo’s Buffalo ‘66 and Disney’s feeble remake of That Darn Cat, Ricci arrived in theaters across the country with adult clothes and adult agendas intent on making you forget she ever played with Uncle Festers and friendly ghosts. Her part as Katrina Van Tassel isn’t much to sink her teeth into, but it cemented her back on the scene for more mature roles.

Filling in around the two leads are a murderer’s row of English theater actors: Miranda Richardson, Michael Gambon, Richard Griffiths, Ian McDiarmid, Christopher Lee, and Michael Gough make up the suspicious upper class in the town of Sleepy Hollow. The haughty Britishness of it all makes it extremely enjoyable to see their heads get lopped off, and Christopher Walken’s murderous Horseman makes it look as easy as a slicing a hot knife through butter.

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NOSTALGIA-FEST OR REPRESSED NIGHTMARE? It’s frightfully fascinating to watch the work of so many talented artists just before ascending towards their respective dates with Hollywood destiny. Sleepy Hollow served as a comfortable stepping stone for a lot of people involved, but it’s neither satisfyingly nostalgic nor a disastrous nightmare. It’s a snapshot from a camping trip, fondly remembered for what it was — eerie, oddly exhilarating, and mercifully short.

RETROGRADE: 6 out of 10

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