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Sleepy Hollow (1999)

TL;DR: Sleepy Hollow (1999) rates 8 out of 10 on the rewatch scale. Tim Burton turns Washington Irving’s ghost story into a gorgeous, gory Gothic horror film, with Johnny Depp as a squeamish New York detective who believes in science and faints at the sight of blood, sent to a village where a headless horseman is lopping off heads. It looks like a nightmare painted in fog and ash. The plot is creaky. The atmosphere is everything. It’s an 8.
Sleepy Hollow (1999)
8 / 10

Official trailer

A Constable of Science

It’s 1799, and Ichabod Crane is a New York constable who believes the police should solve crimes with evidence and reason, instead of torture and confessions. His superiors find him insufferable, so they send him upstate to the Hudson Valley village of Sleepy Hollow, where three people have been found with their heads cut off. Solve that, they tell him, with all your precious science.

The villagers tell him the killer is a ghost: a Hessian mercenary, beheaded during the Revolutionary War, who rides out of the Western Woods at night to take heads. Ichabod doesn’t believe a word of it. Then he sees the Horseman with his own eyes, in the middle of the night, and faints dead away.

Tim Burton made it in 1999, from a script by Andrew Kevin Walker, who’d written Se7en. Burton never made a more purely beautiful film. Washington Irving’s 1820 story is a gentle, comic tale about a nervous schoolteacher. Burton turned it into a blood-soaked Gothic murder mystery, and it works.

I’m a sucker for this movie. Burton’s fog, Walken’s filed teeth and Depp fainting dead away add up to the most fun I get from any Gothic horror of the nineties. It gets an 8 because the mystery falls apart at the end, and that’s the one thing I hold against it.

Depp’s Ichabod

Johnny Depp plays Ichabod as a delicate, jittery man of reason who’s terrified of almost everything: spiders, blood, the dark and the thought that ghosts might be real. He carries a case full of strange homemade instruments, faints at the worst possible moments and screams like a child when things go wrong. His gadgets, a pair of multi-lensed spectacles, a set of surgical tools and a bag of powders, are wonderfully Burtonesque, half science and half toy box, and he uses them with a showman’s pride even when they don’t work.

I adore this Ichabod. Playing the hero as a coward with a good brain is a funny, oddly brave choice.

Depp was deep in his Burton phase, after Edward Scissorhands and Ed Wood, and he makes the cowardice endearing. When he finally does something brave, it means something, because we’ve watched him scream and faint at every turn.

The film gives him a backstory, too: flashbacks to his childhood, and his mother, a gentle woman accused of witchcraft by his fanatical father. It explains his faith in reason and his fear of the supernatural, and it lends the film an unexpected sadness. Lisa Marie plays the mother in dreamlike flashbacks, and those scenes, full of spinning toys and sudden horror, haunt the rest of the film.

For Writers

Ichabod is a coward with a brilliant mind, afraid of spiders, the dark and the sight of blood. His fear makes his eventual courage mean something.

A hero who’s frightened is often more interesting than one who’s fearless. The reader can measure every brave act against the fear it took to overcome, and the courage feels properly earned.

Burton plays Ichabod’s fear for laughs, and then, when it matters, lets him act despite it. The comedy makes the courage stronger, because the audience knows exactly how much it costs him to stand his ground. A fearless hero risks nothing inside. A frightened one risks everything every time he moves forward.

The Village

Sleepy Hollow is a tight little Dutch community run by a handful of powerful elders: the wealthy Baltus Van Tassel, played by Michael Gambon, the stern Reverend Steenwyck, played by Jeffrey Jones, a shifty notary played by Michael Gough and a doctor and magistrate with plenty to hide. Christopher Lee turns up at the start as the New York burgomaster who sends Ichabod away.

The elders welcome Ichabod with forced smiles and dark looks, and every one of them has secrets, and as the Horseman keeps killing, it becomes clear that his victims aren’t random. Somebody is controlling him, pointing him at the people who know too much. The mystery is who, and why, and it leads back through wills, land deeds and old grudges.

The Horseman

Christopher Walken plays the Hessian Horseman in flashbacks, before he lost his head, and he scares me more than anything else in the film: a snarling, wild-haired killer with teeth filed to points, riding a huge black horse and swinging a sword with savage glee. He hardly says a word, and the hissing and the grin do all the work. I’d have happily taken more of him.

After he loses his head, the Horseman is played mostly by a stuntman with a special costume, and the effect is eerie. A headless rider galloping through fog, swinging his blade, is still among the best monsters of the nineties. The beheadings are frequent, sudden and bloody, with heads flying off in all directions, and Burton stages them with a grim, almost comic relish.

The Tree of the Dead

The film’s most famous image is the Tree of the Dead, a huge, twisted, gnarled tree in the Western Woods that marks the Horseman’s grave and his gateway between the worlds. When Ichabod cuts into it, blood pours out. Inside its hollow trunk, he finds the stolen heads of the Horseman’s victims.

It’s pure fairy-tale horror, and the whole look of the film grows from it. Burton and his production designer, Rick Heinrichs, built a whole world around it: a village of grey timber houses, a forest of dead trees, a covered bridge and a windmill, all bathed in fog and drained of color.

For Writers

The Tree of the Dead, bleeding and stuffed with severed heads, sums up the film’s fairy-tale horror in a single image.

A single, powerful central image can define a story’s world and tone. Readers remember a vivid image long after they’ve forgotten the plot, and it can anchor everything around it, from the setting to the theme. Look for the one image that captures your story’s mood and meaning, and build toward it. Place it at a moment of revelation, where it can hold the story’s secrets. Burton puts the stolen heads inside the tree, so the image and the answer arrive together, and neither can be forgotten.

Grey, Fog and Blood

Few horror films have ever looked this beautiful. Emmanuel Lubezki’s cinematography drains almost all the color from the image, leaving greys, blacks and silvers, so that the only strong color is the red of blood when it spurts. The effect is like a Victorian engraving come to life.

The film won the Oscar for art direction, and it deserved it.

The look is the reason this film sits at 8 for me. The village, the woods and the Van Tassel mansion look built for a gorgeous nightmare, and Danny Elfman’s score, all choirs and churning strings, fits them perfectly. I could watch it with the sound off and still be happy.

Katrina

Christina Ricci plays Katrina Van Tassel, the daughter of the richest man in the village, who’s interested in witchcraft and in Ichabod. She’s pale, wide-eyed and mysterious, and for much of the film the audience is invited to suspect her. Ricci is well cast, though the character is a little thin, more a Gothic image than a person.

Casper Van Dien plays Brom Van Brunt, the village bully who loves Katrina, in a role borrowed from Irving’s original story. He’s a big, handsome brute, and he gets one of the film’s best fights, with the Horseman, in a covered bridge.

The Solution

The mystery’s solution, when it comes, is a little convoluted. Miranda Richardson plays Lady Van Tassel, Katrina’s stepmother, and she turns out to be the villain: a witch controlling the Horseman, with a long history of revenge and a twin sister thrown in for good measure. Richardson clearly enjoys the big reveal, cackling and scheming, and she makes a vivid villain.

But the explanation, involving family land, a secret past and a string of murders, is a mess, and my patience runs out with it. It arrives in one long speech that’s hard to follow, and I’d have traded the twin sister for a single clean clue planted early. Burton’s films have never been strong on plot. You watch Sleepy Hollow for the fog, the woods and the Horseman, and you forgive the explanation because everything around it looks so good.

For Writers

The mystery’s solution is delivered in one long, convoluted speech, and it’s hard to follow. The atmosphere holds the film together, and the plot limps along behind it.

A mystery’s solution should be clear and satisfying. If it takes a long speech to explain, the reader may lose track halfway through, and the payoff loses its power.

Plant the clues throughout the story, so that when the answer comes, the reader can put it together quickly. The best solutions feel obvious in hindsight and need only a line or two to deliver.

If you find yourself writing a long explanation, the clues weren’t planted well enough, and the fix belongs earlier in the book. For more, see my article on foreshadowing.

Hammer’s Ghost

Burton grew up on the Gothic horror films of Britain’s Hammer studio, and Sleepy Hollow is his love letter to them. Casting Christopher Lee, Hammer’s great Dracula, as the burgomaster is a deliberate nod. So are the misty forests, the candlelit interiors, the heaving bosoms and the gleeful, theatrical gore.

Michael Gough, who appeared in several Hammer films and played Alfred in Burton’s Batman, is here too. The whole film feels like a lavish, big-budget version of a sixties Hammer picture, made by someone who loved them and wanted to see them done with Hollywood money.

The Windmill

The climax at a burning windmill is another nod to classic horror, echoing the finale of the 1931 Frankenstein. Ichabod, Katrina and young Masbath, the orphan boy who becomes Ichabod’s assistant, are trapped inside while the Horseman hacks his way in, and the windmill goes up in flames.

It’s followed by a wild chase through the woods by coach, with the Horseman in pursuit, and a showdown at the Tree of the Dead. The action is exciting and gloriously over the top, and it gives Depp’s cowardly hero the chance to be brave at last.

Mood Over Mystery

Enjoy Sleepy Hollow for its atmosphere more than its story. The mystery is creaky, the romance is thin and Depp’s comic cowardice sometimes undercuts the tension. The gore will put some viewers off, and the film makes no apology for it.

But the images are unforgettable, the Horseman is a terrific monster and the film has a grisly, playful energy that’s hard to resist. It’s the Hammer horror film Burton always wanted to make, and a fine one.

Craft Note

Craft Note

Atmosphere is how Sleepy Hollow builds its world: fog, grey light, twisted trees and sudden red blood. The mood is so strong that it carries a creaky mystery.

Atmosphere can sustain a story through weaker plotting, but it can’t replace a clear solution.

Invest in the mood of your setting, and make sure your plot’s answers are as clear as your imagery is rich.

A Nightmare in Grey

I give Sleepy Hollow an 8, and I’m fond of every frame of it except the ones where somebody explains the plot. Depp’s squeamish Ichabod, Walken’s snarling Horseman and the best images of Burton’s career make it a treat. The creaky mystery is the only thing keeping it from climbing higher.

Frequently Asked Questions

What is Sleepy Hollow (1999) about?
In 1799, New York constable Ichabod Crane, who believes in scientific investigation, is sent to the village of Sleepy Hollow to solve a series of beheadings. The villagers blame a headless horseman, and Ichabod discovers that the ghostly killer is real and being controlled by someone in the village.
Who directed Sleepy Hollow?
Tim Burton directed Sleepy Hollow, released in 1999, from a screenplay by Andrew Kevin Walker, who also wrote Se7en. It was Burton’s third film with Johnny Depp, after Edward Scissorhands and Ed Wood, and it’s loosely based on Washington Irving’s 1820 story The Legend of Sleepy Hollow.
Who plays the Headless Horseman in Sleepy Hollow?
Christopher Walken plays the Hessian Horseman in flashbacks and in scenes where his head is visible, portraying him as a snarling killer with sharpened teeth. In the headless scenes, the Horseman was largely played by stunt performers wearing a special costume.
Did Sleepy Hollow win any Oscars?
Yes. Sleepy Hollow won the Academy Award for best art direction for Rick Heinrichs and Peter Young. It was also nominated for best cinematography, for Emmanuel Lubezki, and best costume design, for Colleen Atwood. The awards reflect how much of the film’s power comes from its look.
Who is the villain in Sleepy Hollow?
The villain is Lady Van Tassel, played by Miranda Richardson, Katrina’s stepmother. She’s a witch who controls the Headless Horseman through the skull stolen from his grave, using him to eliminate people who stand between her and the Van Tassel fortune.
Is Sleepy Hollow faithful to Washington Irving’s story?
Not very. Irving’s story is a gentle comic tale about a superstitious schoolteacher who may have been frightened off by a rival disguised as the Horseman. Burton’s film keeps the names and setting but turns it into a violent Gothic murder mystery with a real supernatural killer.
Is Sleepy Hollow too scary for kids?
It’s rated R for graphic violence and gore, including many beheadings, and some frightening imagery. It’s best suited to older teenagers and adults. The atmosphere is more spooky than relentlessly terrifying, but the bloodshed is frequent and explicit.

About the Author
Richard Lowe, professional ghostwriter

Richard Lowe is a professional ghostwriter and author with 113+ books authored and 54+ ghostwritten. Before writing full time he spent 33 years in enterprise technology, including 20 years as Director of Computer Operations and Technical Services at Trader Joe's. He writes nonfiction, fiction and memoir, and works with executives and experts on books that build authority.

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Disclaimer

The views and opinions expressed in this blog post are solely those of Richard Lowe and are based on personal experience and research. This content is for informational purposes only and should not be construed as professional legal, financial, accounting, or business advice. Always consult with qualified professionals before making important business or legal decisions. Richard Lowe is not a lawyer, accountant, or licensed professional advisor, and this content does not establish any professional relationship.