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Film / Sleepy Hollow (1999)

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Sleepy Hollow is a 1999 period horror film directed by Tim Burton, interpreting the legend of the Headless Horseman and based loosely upon the Washington Irving story The Legend of Sleepy Hollow. The third film collaboration between Johnny Depp and Burton, the film also features Christina Ricci, Sir Michael Gambon, Miranda Richardson, Casper Van Dien, Jeffrey Jones, Ian McDiarmid, Michael Gough, Richard Griffiths, Martin Landau, and Christopher Walken.

The story centers on Ichabod Crane (Depp), an unconventional police constable sent from New York City to investigate a series of murders in the nearby village of Sleepy Hollow by a mysterious Headless Horseman. The style and themes of the story take inspirations from the late Hammer Film Productions.

Has no relation to the TV show Sleepy Hollow, aside from sharing source material.


This movie provides examples of:

  • Adaptational Attractiveness: Irving describes Ichabod as a very lanky, long-nosed, and odd-looking man in the story, but here, he's played by Johnny Depp. Depp wanted to wear a prosthetic nose, but it didn't work out.
  • Adaptational Badass:
    • The original story makes no mention of how capable the Horseman was as a fighter (he died of a random cannonball tearing his head off). The film version has a reputation as one of the most savage mercenaries to have fought in the War of Independence, goes down in a Last Stand and, thanks to his un-death, spends most of his time in the film acting as a near-unstoppable One-Man Army.
    • Brom Bones is a pretty powerfully-built man in the original story, but he never fights anybody. In this film, he manages a pretty impressive Last Stand against the Horseman with Ichabod's help and would probably have won if not for the whole "undead Implacable Man" thing.
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    • Ichabod himself becomes much braver and more heroic than the cowardly twerp he was in the original story as a constable who is determined to get at the heart of a very grisly murder mystery. He still starts out terrified of the Horseman (when he realizes it's a real ghost) and of spiders, however.
    • Katrina becomes a white witch powerful enough to cast spells that protect those she loves. She's also able to control two panicked horses to outrun the Horseman when he's after her.
  • Adaptational Heroism:
    • The original story's Ichabod was a full-blown Dirty Coward who happens to be a Gold Digger and, while his final fate is left pretty ambiguous, it's harder to dispute that he didn't deserve it. Burton's version, even if quite foppish, is a Cowardly Lion and a determined man of the law.
    • Brom, while still a bit of a jerk and a bully, also proves dedicated and courageous in his defense of the town from the Horseman in this version.
  • Adaptational Job Change: Ichabod is now a police constable instead of a schoolteacher.
  • Adaptation Expansion: This movie gives the original short story more characterization and a more involved plot. Brom, originally Ichabod's love rival in the story (who is also implied to be dressing up as the Headless Horseman), becomes Crane's ally (albeit temporarily) and perishes in single combat against the Horseman.
  • Adaptation Inspiration: As one would expect of a collaboration between Tim Burton and Johnny Depp, this is quite the quirky tale.
  • Adaptation Title Change: The title is shortened from the story The Legend of Sleepy Hollow.
  • Advertised Extra: Christopher Lee gets top billing in the opening credits. He has one scene, which amusingly takes place before the credits.
  • Agent Scully: Ichabod is originally unconvinced of the supernatural elements surrounding the murders. That is until Magistrate Phillipse is decapitated right in front of him.
  • Aluminum Christmas Trees: You might think that Katrina having a book of spells and practicing white magic might be a fanciful historical liberty taken by the filmmakers, especially given the Christian prohibition against witches, however, folk charms and healing, often done within a Protestant Christian context, were not unheard of in rural communities.
  • Ambiguous Situation: The church scene. Was the Horseman prevented from entering the church due to it being hallowed ground or Katrina's protection spell?
  • An Arm and a Leg: The Hessian cuts off an American soldier's arm during his Last Stand.
  • Anti-Villain: The Horseman technically. He's only killing because Lady Van Tassel is summoning him from the grave and making him do her bidding. When the head is returned, he happily goes into the afterlife.
  • Artistic License – Biology: Ichabod is sprayed in the face with blood when he cuts into a decapitated cadaver. Not only would a long-dead corpse have no blood pressure, but a headless one wouldn't really even have any more blood. It's probably an exceptionally morbid example of Rule of Funny, though (he is, after all, doing an autopsy on someone whose cause of death is quite obvious). There is an attempted hand wave for the latter case, as it's said the Horseman's blade cauterizes the wounds of the heads he cuts off.
  • Ax-Crazy:
    • Lady Van Tassel. At one point with a literal ax (even though sneakily enough, in the back)!
    • The Headless Horseman has an ax and was a berserker with a love of carnage in life.
  • Bait-and-Switch Gunshot: Used when Jonathan Masbath attempts to snipe the Horseman. The shot is heard from a distance and the horse neighs, suggesting the Horseman was taken out. The scene then cuts to Masbath running down the road as fast as he can, his shot having failed.
  • Best Served Cold: Lady Van Tassel had been planning her revenge since childhood.
  • Better to Die than Be Killed: Notary Hardenbrook commits suicide by hanging because he expects to be the Horseman's next victim otherwise.
  • Big Bad: The Headless Horseman terrorizes Sleepy Hollow by decapitating its citizens, making him responsible for the murders that Ichabod is investigating, but at the end it turns out he isn't acting out of his own will, but is controlled by an important figure in the village, Lady Van Tassel, for the sake of her revenge against the Van Tassels and Van Garrets for leaving her homeless, and securing herself power and fortune.
  • Bitch in Sheep's Clothing: Lady Van Tassel only acts nice in public and has successfully been hiding for decades that everything she's been doing since she's (back) in the town is to get revenge.
  • Black Comedy: Though the film is mainly action horror, it has moments of this, mostly involving Ichabod doing darkly funny things himself or having such things happen to him.
  • Blade Lock: The Horseman was beaten while alive when his weapons were caught in a bind and another soldier stabbed him.
  • Bloodier and Gorier: The original story wasn't bloodless, but the Horseman being headless was the goriest thing in it. This movie has loads of decapitations as well as other forms of bloody deaths. It's definitely the bloodiest film in Burton's filmography except Sweeney Todd.
  • Bloody Handprint: Lady Van Tassel smears one on Reverend Steenwyck's back during sex in the woods.
  • Bloody Hilarious: Tim Burton actually tried to find as many excuses as possible to have Ichabod sprayed in the face with blood. Later becomes less funny, when the trope is applied in Ichabod's backstory... as he's a young child and the one bleeding all over him is his recently murdered mother.
  • Blood Knight: The Hessian, in life, was a mercenary who joined the war of Independence purely for the fun of killing.
  • Body Horror: At the end, when the Horseman's skull morphs into a human head, including a brief Wild Take.
  • Cassandra Truth: Amusingly subverted after Ichabod encounters the very real horseman for the first time. The townspeople already knew he existed and reiterate to Ichabod that the entire reason he's here is to deal with the horseman.
  • Catapult Nightmare: Ichabod. A lot.
  • Chairman of the Brawl: Killian throws a chair at the Horseman when the latter bursts into his house. The Horseman just deflects it with his axes.
  • Chekhov's Gun:
    • Ichabod's scars on his hands. When he's leaving Sleepy Hollow after believing Katrina is the cause of all the chaos, he looks at them, recalls the scar on Lady Van Tassel's hand, and is able to put two and two together; the cut on the body believed to be Lady Van Tassel was made postmortem, and she faked her death.
    • Katrina gives Ichabod a book, which at first seems just like a gift, but later is pivotal to the plot in two ways.
      • Ichabod is saved from being shot because he wears the book in his jacket.
      • It is reading in this book (it's Katrina's book of spells) that makes Ichabod realize that Katrina is not an evil witch, as he then thought, but a good one; and that she loves him, because he reads that her spell was "to protect a loved one".
  • Chekhov's Gunman:
    • The two little girls that the Horseman comes across as he's escaping the army. At first, they just seem like a random inclusion, but end up integral to the story.
    • Sarah the servant girl is introduced in a tryst with Dr. Lancaster; Lady Van Tassel reveals that she used this information to blackmail him. Near the end of the film, she's apparently run off, but in fact Lady Van Tassel murdered her in order to fake her own death.
    • Beth Killian is introduced as a kindly midwife in the town. When it was discovered the Widow Winship was pregnant, she knew the secret and confided in her husband - sealing their fates in the murder plan.
  • Children Are Innocent: Averted with Lady Van Tassel when she was a little girl and apparently cruel from the start.
  • Coitus Uninterruptus: Twice. When Ichabod arrives at the Van Tassels' party, he stumbles upon the sight of an elderly man and a young woman engaged in passionate kissing (later revealed to be Dr. Lancaster and the Van Tassels' young buxom servant girl Sarah). The second time, Ichabod follows a cloaked figure into the woods and discovers Reverend Steenwyck and Lady Van Tassel engaged in sexual intercourse.
  • Connected All Along: Those two girls the Horseman encounters before his death? Turns out they are a young Lady Van Tassel and her sister, who seem to be directly responsible for the Headless Horseman even existing in this continuity.
  • Cool Horse: Next up on Pimp My Horse, we examine the Hessian's ride, Daredevil.
  • Cool Sword: The Horseman has a totally sick black-bladed one with a snake's-head pommel.
  • Costume Porn: The film's costume design didn't get an Academy Award nomination for no reason. The dresses are amazing.
  • Cow Tools: The autopsy sequence. Ichabod hand-waves it by saying some of the tools are of his own design.
  • Cranium Chase: The Headless Horseman is forced to kill people until he gets his own head returned.
  • Creepy Child: Lady Van Tassel promised her soul to the Devil as a child, for revenge on those who drove her family to poverty.
  • Darker and Edgier: This interpretation of The Legend of Sleepy Hollow is much more legitimately frightening than the original, most notably thanks to the very real Headless Horseman killing people in cold blood. There are darker themes in this adaptation as well, ranging for sexual desire to black magic to religious fanaticism. Of course, we can expect nothing less from Tim Burton.
  • Dark Fantasy: The film's tone is close to that of a dark fairy tale, as it involves Wicked Witches and black and white magic in addition to the murder plot.
  • Dark Is Not Evil:
    • The Witch of the Western Woods just wants to help, and gets killed for her trouble.
    • The Hessian might be an example. He was a vicious soldier when he was alive, but instead of killing the two little girls who could give him away, he simply shushed them. While he's certainly killing lots of people now, he's only doing it because Lady Van Tassel is controlling him. So it's more Dark Is Not Completely Evil. He certainly cares for his horse, stroking it when it's dying and happily patting it when they're reunited. In fact, while he was ruthless, he isn't seen killing anyone unarmed while alive, and the moment he gets his head back, he only kills the one responsible for his pain before leaving.
  • Dead Star Walking: Martin Landau (Peter Van Garrett) is murdered by the Horseman before the film even reaches two minutes.
  • Dead to Begin With: Ichabod and Young Masbeth try to get rid of the Horseman by actions, such as setting a windmill he is in on fire, that would kill a normal human, but then lampshade that isn't of much use against someone who's already dead.
    Young Masbeth: Is he dead?
    Ichabod: That's the problem; he was dead to begin with.
  • Death by Adaptation: Brom is killed when trying to fight the Horseman off.
  • Death by Sex: Three characters meet their demise this way.
    • The busty young servent girl Sarah meets her demise via having her head decapitated and Lancaster gets his head bashed in with a large crucifix not long after their steamy affair together. Courtesy of Lady Van Tassel's manipulation and blackmail.
    • After having rough animalistic extramarital sex with Lady Van Tassel in the woods, Reverend Steenwick gets shot in the chest by a panicked Lord Van Tassel when he tries to keep Lancaster silent about Lady Van Tassel's manipulations of them.
  • Death of a Child: Tim Burton says in the DVD Commentary that he dislikes it when children are always spared from danger in horror films.
    • The Horseman beheads the Widow Winship and impales her unborn fetus.
    • Thomas Killian is dragged out of the cellar by the Horseman and then beheaded.
    • The Horseman does spare those two little girls in his introductory scene, but he winds up regretting it. Big time.
  • Deliberately Monochrome: All the colors are dulled except for the blood.
  • Demoted to Extra: Extra might be going a little far, but Brom's role as Ichabod's rival is massively downplayed. He's only in a handful of scenes, not really a threat to Ichabod and Katrina, and dies halfway through.
  • Disposable Pilot: The first person killed in the whole film is Peter Van Garrett's driver.
  • Dragged Off to Hell: Lady Van Tassel's fate with the Hessian at the end of the movie.
  • Driven to Suicide: Hardenbrook hangs himself because he can't live with his knowledge of the conspiracy.
  • Dual Wielding: Used by the Hessian, to great effect. Brom, not so much.
  • Dwindling Party: When Ichabod first walks through Sleepy Hollow, he sees a lot of the townspeople who will figure into this mystery. By the end of the movie, most of those townspeople will be dead.
  • Eagle-Eye Detection: Ichabod's preferred method for solving the streak of murders.
  • Eerie Pale-Skinned Brunette: It's a Tim Burton film, so obviously Ichabod and the Hessian fit this trope.
  • Even Evil Has Loved Ones: The Hessian is a bloodthirsty killer, but he seems to be very affectionate toward his horse.
  • Even Evil Has Standards: The Horseman, pre-mortem, was an extremely vicious soldier who reveled in carnage... but at the same time, he was not one for killing children. His bit of kindness or mercy comes back to bite him in the ass, especially when we learn that a young Lady Van Tassel intentionally gave him away so she can perform her deeds in the film, as she narrates to Katrina.
  • Evil-Detecting Dog: Animals tend to flee whenever the Horseman shows up, such as sheep and in the case of Jonathan Masbeth, a herd of deer.
  • Expository Hairstyle Change: After she's revealed to be evil, Lady Van Tassel's hair is loose, while before she always wore it up.
  • Faint in Shock: The 'cowardly' Ichabod Crane is the hero and can't very well show true cowardice, so he tends to stick out any dangerous situation (like, say, any time the Headless Horseman shows up and makes with the headchopping) and then pass out once it's over.
    • Played straight with Katrina, who faints twice over the course of the film, first when her father is impaled by a fence post in front of her, and then when her stepmother (believed to have been killed) reveals herself alive and well.
  • Fairy Tale Motifs: The plot is orchestrated by a Wicked Stepmother who herself ended up in servitude.
  • Faking the Dead: Lady Van Tassel fakes having died of decapitation by the Horseman, by killing an unfortunate maid and substituting the headless body of that girl for that of her own corpse.
  • Fan Disservice: The sex scene between Reverend Steenwyck and Lady Van Tassel. Besides such taking place in the eerie cold woods and his being a slightly obese and unattractive man with a evil attractive married woman, the animal noises he makes and the way she slices open her hand and wipes blood on him during intercourse only adds to it.
  • Fanservice: Burton's girlfriend at the time, Lisa Marie, shows up in some dream sequences as Ichabod's gorgeous mother. The script actually called for a scene where she dances while loosening her top until she's pretty much topless.
  • Fate Worse than Death: Lady Van Tassel is still alive when the Horseman takes her into the Tree of the Dead. Not only is she taken to Hell (presumably forever), but the Horseman is furiously mad at her, and really not someone you want to piss off...
  • Flaming Sword: Not actually in flames, but the Horseman's sword is so hot from the fires of Hell that it cauterizes any wounds it inflicts.
  • For the Evulz: The Hessian/Headless Horseman worked for the British rather for the fun to slaughter than for money.
  • Foreshadowing:
    • The fact that the Horseman is following orders and hunting down specific targets, and not just a mindless killer who slaughters everything he can is foreshadowed when he initially spares both Ichabod and Brom.
    • When Ichabod shares this realization with Baltus, Doctor Lancaster clearly gets an Oh, Crap! expression on his face, suggesting he already knows how the Horseman is operating.
    • Katrina points out a decorative archer on what's left of the fireplace when she and Ichabod first visit her childhood cottage. It actually figures into the Big Bad's Motive Rant in the climax.
    • When we see the supposed "evil eye" drawn by Katrina at the church, it's notably drawn in pink chalk. Such a color motif hints that its intentions are more benign than it appears.
    • Lady Van Tassel gets a cut on her hand. Her knowing how to treat the wound with local flowers foreshadows that she is a witch, and the fact that she was seen cutting it herself in ritualistic fashion while having extramarital sex shortly before should tell the audience she is not a good witch.
  • Freudian Excuse: Lady Van Tassel does actually have a fairly good reason to hate the Van Garretts and the Van Tassels. Both of them seized her family's land and left her, her mother and her twin sister to starve; no one in the town would take them in and the mother died within a year, leaving her daughters completely destitute and forced to live in the woods.
  • Freudian Excuse Is No Excuse: That said, Lady Van Tassel's excuse does not justify her murdering her own sister, or Masbeth the Elder, or the servant girl out of pure spite, or the midwife who knew Widow Winship had been pregnant, or her husband and young son; nor does it excuse her greed, which makes her just as bad as the families she was seeking revenge against, and probably even worse.
  • Genre Throwback: Tim Burton imagined the film as one to Hammer Horror, particularly Doctor Jekyll and Sister Hyde. Casting Hammer veterans Christopher Lee and Michael Gough in small roles was a deliberate reference. The film was even shot in England rather than New York, where it was set.
  • Good Hair, Evil Hair: Lady Van Tassel has her hair up while pretending to be good. When she's evil, she wears her hair down.
  • Gory Discretion Shot: Used when Peter Van Garrett is decapitated, with his blood splattering on a nearby scarecrow.
  • Gothic Horror: There are a few scenes highlighting the eeriness of the Van Tassel family house, particularly when Ichabod in the shadows watches someone sneaking out at night.
  • Groin Attack: The Magistrate's head hits Ichabod in the groin when he is decapitated.
  • Half the Man He Used to Be: Brom is literally cut into two pieces (through the abdomen) by the Headless Horseman.
  • Headless Horseman: In this film, he's a former mercenary who died by decapitation and is later summoned from the dead to decapitate other people until his own head is returned to him.
  • The Heavy: The Horseman to Lady Van Tassel. He is definitely the main threat to the other characters and is only working for her because she has his skull.
  • Heel–Face Turn: The Horseman. Once he gets back his head, he gives a more-than-deserved punishment to Lady Van Tassel (probably realizing she's the one who got him killed long ago and the one who forced him to commit decapitations), biting her while kissing her, and dragging her to Hell.
  • He Knows Too Much:
    • Jonathan Masbath and the Killian family are killed because the former was a witness to the secret marriage between Van Garrett and the Widow Winship, and Beth Killian told Lady Van Tassel that she knew the Widow had been pregnant in front of her husband.
    • Lancaster is killed by Steenwyck when the former tries to confess Lady Van Tassel's conspiracy.
  • Hellgate: The Tree of the Dead is where the Horseman travels between Earth and the underworld.
  • Hellish Horse: Daredevil, the Hessian's horse. Though in this case, it's literally being summoned from Hell (along with the Horseman himself).
  • High Collar of Doom: The Headless Horseman wears one of these to go with his Badass Cape. On a meta note, it was a pain to film and the collar was essentially made into a CGI object which was matched with his movements.
  • Hoist by His Own Petard:
    • The Horseman was decapitated with his own sword, instead of having his head blown off by a cannonball.
    • If Lady Van Tassel hadn't cut her hand during sex with Reverend Steenwyck (thus meaning she had to make a similar cut on the hand of Sarah, the servant girl, whose body she was using to fake her death), Ichabod wouldn't have made the connection with his own scars and realized something was up. Namely that, when the cut was made, the headless woman was already dead.
  • Holiday Motif: The film is loaded with Halloween Friendly imagery. The misty, gothic farming village, the creepy Hammer Horror inspired visuals, and even Jack-O-Lantern headed scarecrows. And that’s before Walken’s Horseman makes his appearance.
  • Holy Burns Evil: The Horseman can't enter the hallowed church grounds for this reason. His horse refuses to even set foot in it, and when he throws his ax into it, it immediately disintegrates. The Horseman works around this by tying a piece of the church fence to a rope, using it to impale Baltus and drag him out before beheading him. Invoked Trope since Katrina had actually cast a protection spell to keep him out of the church.
  • Hot Witch:
    • Ichabod's mom, although her status as a witch is debatable. She was associated with magic.
    • Lady Van Tassel is an evil example. She's very attractive and a mistress of black magic.
    • Katrina practices witchcraft, since she is seen making a potion and chanting a spell when Ichabod falls ill. She goes more toward Cute Witch.
  • Impaled with Extreme Prejudice:
    • Baltus Van Tassel during the church attack. The Horseman grabs a fence post and rope, throws it through the window to spear Baltus, drags him to the fence, and then decapitates him.
    • The fate of Ichabod's mother, inside an iron maiden.
  • Imperiled in Pregnancy: One of the Horseman's victims is the Widow Winship, who was pregnant. The Horseman beheads both her and the baby.
  • Impossibly-Low Neckline: Ichabod's mother in the flashbacks, played by Burton's then-wife Lisa Marie Smith. Combined with Of Corsets Sexy, you may find yourself thinking more on the chances of a nip slip than the somber mood of the scene. See here.
  • Impoverished Patrician: Lady Van Tassel's family was forced into this by Peter Van Garrett, who forced them off their land when their father died, and Baltus who took said land for himself. This is why she used the Headless Horseman for revenge.
  • Info Dump: There's a particularly awkward conversation in the movie's first act in which Katrina explains her family's history to Ichabod. Christina Ricci does her best with it, but it inevitably sounds like a recitation of information that'll be important later.
  • Informed Attribute: Katrina loves her father enough to burn evidence she thinks might be used against him, and tells Ichabod that there was no danger for her in riding through the Western Woods if it were her own father who summoned the Horseman—and yet at no point do we ever see father and daughter have any meaningful interaction throughout the course of the film. Apart from her screams of terror when he is killed.
  • The Ingenue: Katrina is a subversion. While she has the Angelic Beauty and kindness to everyone, she's much smarter and braver than she appears. Ichabod suspects she's actually the one summoning the Horseman, hiding behind the facade of being an Ingenue, but she's not.
  • In Name Only: Washington Irving's story is a humorous and satirical story about an obnoxious Yankee schoolteacher who invades a Dutch-American community, makes a nuisance of himself, and gets run out of town by the clever ruse of a local rowdy. It's much more about clashing cultures in early America than anything else. The film, however, is a supernatural thriller about a science-minded inspector who must solve a mystery to defeat a supernatural enemy, with the major themes being science, superstition, and sexism.
  • In the Back: Brom Bones throws a knife into the Horseman's back, which Ichabod follows up by stabbing the Horseman in the back with a scythe. Neither does anything.
  • Iron Maiden: Ichabod remembers that his mother was locked inside an iron maiden by his father when he thought the free-spirited woman was a witch.
  • It's Going Down: The windmill. Monster movies hate windmills. This was not an uncommon fate for windmills of the time, minus the hell-monster part. Flour is surprisingly flammable.
  • It's Quiet… Too Quiet: Note to city slickers: Forests are supposed to be noisy.
  • Killed Mid-Sentence: Dr. Lancaster tries to reason with Baltus, saying "We were devilishly possessed by one who...", but Reverend Steenwyck hits a wooden cross on his head before he can finish.
  • Large Ham:
  • Laser-Guided Karma: Anyone decapitated by the Horseman is potentially condemned to Hell, since he brings their heads with him to the Tree of the Dead in his journey back to the underworld. When he has his own head back and Lady Van Tassel in his power, the Horseman takes her with him to Hell while she's still alive. Albeit not for very long.
  • Last Grasp at Life: How Lady Van Tassel's hand appears in the Tree of the Dead when the Hessian drags her to Hell. Interestingly, the way her arm is at first positioned with her palm up and fingers stretched out towards freedom becomes even creepier, as the muscles relax in death and her fingers curl up in a 'come hither' gesture.
  • Last Stand: The Horseman was killed in one of these while being hunted by American soldiers close to the outskirts of Sleepy Hollow. He managed to kill at least four men before being brought down.
  • Left Hanging: The film ends with Ichabod, Katrina, and Young Masbath arriving in New York, ready to start their new lives together. Without providing an answer to how they're actually going to explain what happened to the Burgomaster and High Constable. Technically, Ichabod did solve the case, but there's no one to face justice...
  • Light Is Not Good:
    • Ichabod's father's eye-searingly white church hides a dungeon filled with torture devices.
    • Played with in regards to Katrina. As she is the only character to dress in light colors and ride a white horse, her significance is clear immediately to a Genre Savvy viewer. When combined with her witchcraft, this makes her legitimately suspicious by the time Ichabod suspects her of controlling the Horseman. In the end, though, she turns out to be good after all.
      Ichabod: [to Young Masbath] Villainy wears many masks, none of which so dangerous as the mask of virtue.
      • Which he's almost certainly thinking about his pious father when he says.
  • Lodged-Blade Recycling: Brom Bones throws a knife into the Headless Horseman's back, but he pulls it out and throws it into Brom's thigh.
  • Loophole Abuse: Sure, the Headless Horseman can't enter hallowed ground, but that doesn't mean he can't tie a piece of the fence to a rope, swing it into the church to impale his next victim, and drag him out before beheading him.
  • Lovecraft Country: The town of Sleepy Hollow and its surrounding spooky woods comprise a spiritual cousin, at least.
  • The Man Behind the Man: Lady Van Tassel is the one controlling the Horseman and ordering him to kill.
  • Men Are the Expendable Gender: Averted throughout; the Horseman chops off as many women's heads as he does the men.
  • Mood Lighting: The entirety of the movie, except the ending scene, is shot with a creepy blue filter. The "red" blood is actually orange.
  • Mood Whiplash:
    • The horror tone of the scenes with the Horseman are interspersed with the darkly comedic scenes with the bumbling Ichabod Crane.
      Roger Ebert: It's as if the Horseman gallops ahead in a traditional horror film, and Depp and Burton gallop right behind him in a satire.
    • The deaths of the Killian family. Up until this point, the sight of people getting their heads sliced off has been enjoyable in a funny/gruesome sort of way, but the deaths of kind-hearted Killian, his wife, and their young son are treated as a genuine tragedy.
  • Mr. Exposition: When the true villain is finally revealed, she goes into a long, long Infodump of raw, untreated exposition that details her entire scheme in agonizing detail. It doubles as a Motive Rant, but despite all the Evil Gloating that goes on, it's a Justified Trope considering Lady Van Tassel has already called for the Headless Horseman, and so loses nothing by spelling out in great detail the whys and wherefores of the plot.
  • Ms. Fanservice: Christina Ricci is absolutely smoking hot in this film. She's not a filler character, but her deep cleavage makes her fit the trope.
  • Mythology Gag: Brom's fake Horseman prank closely mirrors Ichabod's encounter with the Horseman in The Legend of Sleepy Hollow.
  • Near-Miss Groin Attack: When Magistrate Phillipse is killed by the Horseman, his head spins on his body before falling off and rolling down the slope towards Ichabod. The head comes to rest between Ichabod's legs, and the Horseman retrieves it by spearing it on his sword as he rides past, the blade striking inches from Ichabod's crotch. Ichabod faints.
  • Neutral Female: During the climax, when Ichabod and Lady Van Tassel are fighting over the Horseman's head, Katrina...just stands and watches them, as opposed to hitting her stepmother like Young Masbath or running to get the skull. As a result, she's grabbed by the Horseman and only saved from beheading in the nick of time.
  • Never Trust a Trailer: The second trailer seems to suggest that Ichabod and his family were attacked by the Headless Horseman when he was a child, which isn't the case in the finished film.
  • Noble Demon: The Horseman, both in his past life and his ghost life.
  • Non-Action Big Bad: Lady Van Tassel, who rules Sleepy Hollow secretly behind the scenes through the Headless Horseman. Justified as they had to remain anonymous. They do get their hands dirty by murdering Sarah the servant girl and the crone in the western woods by hand, and shooting Ichabod in the climax but it still pales in comparison.
  • No Name Given: Lady Van Tassel's first name is never revealed. According to the family tree visible in the movie, her name is "Mary Preston." However, since she later reveals that her family name was Archer, it's possible that she went under a completely different pseudonym when she became a caregiver and later wife to Baltus.
  • Non-Dubbed Grunts: Christopher Walken's yells as The Horseman are retained in the film's foreign-language dubs.
  • Non-Malicious Monster: The Horseman. He only kills when Lady Van Tassel orders him to. All he wants is to have his head back and finally rest in peace.
  • Nothing Is Scarier: Lampshaded in the woods.
  • Obvious Villain, Secret Villain: The Headless Horseman is going around killing the residents of Sleepy Hollow to recover his head after he was decapitated by a cannonball in the Revolutionary War. What Ichabod and the town of Sleepy Hollow don't know at least until much later is that the true mastermind behind the Horseman's revenge is none other than Katrina's stepmother Lady Van Tassel.
  • Oedipus Complex: Ichabod falls like a brick for the cute witch Katrina. His mother was "an innocent child of nature" "condemned, murdered to save her soul" by his father, a "Bible-black tyrant hiding behind a mask of righteousness." That won't happen again. Ichabod is a Man of Reason who rejects the intolerance of the Church and honors the gentle Katrina for her compassion.
  • Off with His Head!: The Movie. When the Headless Horseman is after someone, he ends up decapitating the victim and brings the head to the cursed tree he spawns from. He loved killing this way he was a Hessian mercenary during the American Revolution, and himself perished this way.
  • Oh, Crap!: Lady Van Tassel gives a particularly great one when she realizes in whose arms she just woke up after the final showdown.
    • Ichabod when he first sees the Horseman in Sleepy Hollow and flees for his life; really, it's just Brom and his friends playing a prank on him.
  • Ominous Fog: Rolls in and puts out the torches before the Horseman comes riding in.
  • One-Woman Wail: A few songs in the soundtrack feature a single woman wailing with great effect. Special notion to the gentle wail during Ichabod's memories of his mother and the same wail with a much more unsettling feeling in the woods.
  • Out-of-Character Alert: When everyone has been assuming that the Horseman has just come back from Hell to go on a rampage, when Ichabod witnesses the Horseman not bother fighting Brom until Brom forced the battle himself, he realises that the Horseman is under some form of control and is killing people on behalf of a living soul.
  • Papa Wolf: Mr. Killian tries to fight the Horseman to save his family, but the Horseman kills him before going after his wife and son.
  • The Place: The movie is set in Sleepy Hollow as you would expect from an adaptation of a famous American story.
  • Pet the Dog: The Headless Horseman clearly adores his horse Daredevil. When it's shot at the beginning of the movie, he reacts with grief (indeed, had he not stalled to comfort it, he probably would have gotten away), and when they are reunited at the end of the film, he gives it a genuine and surprisingly sweet smile.
  • Pimped-Out Dress: Sleepy Hollow is a well-off town, so fancy dresses are the norm. Even in a flashback, two girls kicked out of their home are forced to wear fur-trimmed winter ballgowns while gathering firewood.
  • Police Brutality: From the beginning of the movie, when two policemen bring in a badly beaten man arrested for burglary. It's heavily implied that they beat him up.
  • Poor Communication Kills: Well, not "kills," but if Magistrate Philipse had said to Ichabod "Widow Winship was pregnant," instead of "There are five victims in four graves," he would have spared the poor constable some very messy work.
  • Portal Cut: The Tree of the Dead only lets souls through; any material objects, such as the victims' bodies, get compressed inside the tree trunk instead.
  • Protective Charm: Katrina's pentagram; though Ichabod correctly interprets it as a sign that Katrina practices witchcraft, he instead concludes that this must mean she is behind the murders and doesn't discover that it is a protective charm until he reads her book while leaving Sleepy Hollow.
  • Psycho for Hire: The Hessian worked for the Redcoats, not for money but for the love of killing.
    Baltus: Unlike his compatriots, who came for money, the Horseman came for love of carnage.
  • Punch-Clock Villain: The Headless Horseman is revealed to be this. He's actually manipulated by Lady Van Tassel to kill for her own revenge and, unlike in his previous life, he feels no pleasure in the killings. Moreover, you can see that when he has killed his specific targets, he simply heads back to the forest, not caring of anyone. Even when Brom attacks him, he simply overpowers him and begins to leave, showing that he is not interested in killing him. Unfortunately, Brom is too brash for his own good and so he ends up cleaved in twain.
  • Red Herring: There are clues pointing to both Baltus and Katrina as the culprit before Ichabod finally twigs upon the truth.
  • Right for the Wrong Reasons:
    • Ichabod starts his investigation firmly believing that the Horseman is a man of flesh and blood, and that the Horseman has a human reason to be running around killing people. He's wrong about the Horseman being a human being, but he's right about there being a human motive... namely, the motive of whoever has managed to summon the Horseman from the grave. He also suspects that the culprit is hiding behind "the mask of virtue". He's right but it's not Katrina - rather her stepmother.
    • Young Masbath finding a chalk symbol drawn under Ichabod's bed leads the boy to declare "someone is casting spells against you". Someone is casting spells - in this case Katrina - but it's a spell of protection.
  • Scary Scarecrows: Plenty of them all throughout Sleepy Hollow, but most notably the familiar pumpkin-headed scarecrow at the very beginning of the film.
  • Scary Teeth: The Horseman has filed his teeth to sharp points to add to the ferocity of his appearance.
  • Seeking Sanctuary: The Headless Horseman cannot enter Holy Ground, so fleeing there almost works... See Loophole Abuse, above.
  • Shout-Out:
    • The film opens with a man passing a cornfield that has a scarecrow standing up in it. Some may need a double take, but others will recognize it immediately from one of Tim Burton's other films.
    • The Adventures of Ichabod and Mr. Toad has at least three: The toads by the bridge croaking "Ichabod", a (fake) Horseman throwing a flaming pumpkin on Ichabod (and coming towards the camera), and Ichabod suddenly realizing he's on Daredevil backwards. The fact that Brom disguises himself as the Horseman to freak out Ichabod.
    • When Ichabod borrows a horse from Killian, he's told its name is "Gunpowder," just like his borrowed horse in Irving's short story. Likewise, the Hessian's horse is called "Daredevil" which, in the short story, was the name of Brom's horse.
    • At the end of the film, Ichabod says "The Bronx is up, the Battery's down, and home is this way."
  • Sinister Minister:
    • Reverend Steenwyck has no problem with Lady Van Tassel slicing her hand, smearing him with her blood, and drinking it while they're having a roll in the woods. And he later strikes Dr. Lancaster dead for saying too much to Baltus.
    • Ichabod's dad, who hated witches and figured the only way to save his wife's soul was to kill her in one of many torture devices he keeps in his church. In his dreams, Ichabod closely associates the murderous Horseman with his "Bible-black tyrant" father.
  • Sinister Scythe: When Ichabod and Brom tag-team the Horseman, the former uses a scythe while the latter carries a pair of sickles. Ichabod manages to stall the Horseman by stabbing him in the back, forcing him to stop and pull it out before going on the offensive again.
  • Skepticism Failure: Ichabod refuses to believe that there is a murderous ghoul behind the barrage of grisly deaths up until he sees the actual Horseman coming to get a victim right in front of him.
  • Slasher Film: An unusual example. It's not only a gothic horror movie adaptation of a well-known American folk tale but it's also a Period Piece set in small-town New York after the Revolutionary War.
  • Snow Means Death: It was snowing when the Hessian became the Headless Horseman.
  • Sole Survivor: At the end of the film, Baltus and Mary Van Tassel are dead, leaving their daughter Katrina as the last living member of the Van Tassels.
  • So Much for Stealth: Played wonderfully straight when the Hessian who later becomes the Headless Horseman is escaping through the woods from Revolutionary War soldiers. He encounters two girls gathering firewood and cautions them to silence with a finger to his lips. Without changing expression, one of the girls deliberately snaps the stick she's holding, drawing the soldiers in their direction.
  • Spanner in the Works: Ichabod ends up being this twice for the Big Bad. First, he and Young Masbath spot Lady Van Tassel having a tryst with Reverend Steenwyck, during which she cuts her hand; she has to add a similar cut to Sarah's hand after she murders her. Then Ichabod, after having examined the body, has a "Eureka!" Moment and realizes the wound on the body was made after the woman had been beheaded, meaning he figures out Lady Van Tassel's plot and is able to get to the windmill in time to help Katrina and Young Masbath.
  • Spectacular Spinning:
    • It's mentioned on the DVD that Tim Burton specifically asked the special effects guys to make the heads of the victims of the Headless Horseman pop off and spin a few times after being beheaded. Cue demonstration of said special effects.
    • Ichabod's mother levitates and spins in the woods in one of his childhood flashbacks.
  • "Spread Wings" Frame Shot: When the judge admonishes Ichabod Crane at the beginning of the film and sends him to the titular town, he appears to have wings. Those wings belong to a statue of an eagle behind him. Eagle is an emblem of America, but it's also an intimidating bird of prey.
  • Stylistic Suck: The "Horseman" who attacks Ichabod one night is revealed to be Brom Bones, who is wearing a cloak atop his head with padding around the head doubling as the "shoulders". VFX supervisor Jim Mitchell mentions in a documentary about the making of the film says that this was a common method of portraying the Headless Horseman in past adaptations, but this did not hold up as a good effect over time due to obvious Off-Model points, namely the arms coming out where the "waist" would be.
  • Supernaturally Marked Grave: The Tree of the Dead grows up over the Horseman's resting place, which also doubles as a portal into Hell from which he emerges on Lady van Tassell's bidding.
  • Suspect Existence Failure: A variant in that everyone knows that the Headless Horseman is doing all the killing, but they're trying to find the person controlling him. Lady Van Tassel decapitates a maid to serve as her corpse.
  • Take a Third Option: Katrina makes a spell to keep the Horseman from entering the church, which keeps her father safe. The Horseman would fail his mission if he can't get to Baltus, so he uses a fence post as a harpoon to drag Baltus out of the church and take his head.
  • Tap on the Head: During the climax, Young Masbeth hits Lady Van Tassel over the head with a heavy piece of wood, knocking her unconscious. This allows Ichabod enough time to retrieve the Horseman's skull and return it.
  • The Three Faces of Eve: The three prominent female characters. Katrina, as the youngest, is The Child; she's an Ingenue and rather naive but very trusting. Ichabod's mother is The Wife; in addition to being very maternal, she's shown to be caring and nurturing. Lady Van Tassel is the Seductress. She seduced her way into becoming the Van Tassel matriarch and has a fling with Reverend Steenwyck.
  • Throwing Your Sword Always Works: Subverted by the Horseman when he tries to figure out how to get Baltus Van Tassel. He throws his axe at the church fence, but the holy aura surrounding the church melts it.
  • Took a Level in Badass: After he recovers from his minor hysteria after seeing the Horseman with his own eyes, Ichabod renews his determination to finish the case; in short, as he puts it, pitting himself against a murdering ghost.
  • Torture Cellar: Ichabod's father killed his free-spirited wife in one of these by locking her in an iron maiden.
  • Town with a Dark Secret: The general public just knows that there are several murders in Sleepy Hollow. The town's council knows that it's a ghostly Headless Horseman going around doing the killing and also who's controlling him.
  • Troubled Backstory Flashback: While Ichabod is having a nightmare about his childhood, we see what happened to his mother, and this story is quite a tearjerker.
  • Unholy Matrimony: When the Hessian, now in possession of his head that was taken from him by Lady Van Tassel, gives her a squick-filled kiss as he drags the both of them into Hell to spend eternity.
  • The Vamp: Lady Van Tassel, who manages to seduce Reverend Steenwyck into her service.
  • Villainous Valour: Brom, who spends most of the film as a jealous Jerkass to Ichabod, fearlessly faces an invincible undead headless warrior using a musket and then a pair of sickles and actually has the Hessian on the defensive for most of their fight until his guard slips and he becomes Half the Man He Used to Be.
  • Villainy-Free Villain: The Horseman himself, oddly enough. Baltus Van Tassel describes him as a Psycho for Hire who took part in the Revolutionary War to satisfy his bloodlust, and thus one would assume he was an evil sadist. But despite his motives, we never see him cut down anyone during the war who wasn't an enemy soldier. He spares the lives of two little girls who cross his path, even after one alerts the enemy to his presence. In the present day, when he's resurrected as the Headless Horseman, it's established that Lady Van Tassel is controlling him via supernatural means, and he only kills the people she forces him to. When he is finally restored to his original form and freed from Lady Van Tassel's control, he leaves the heroes alone, takes his revenge on Lady Van Tassel, and promptly departs for the afterlife.
  • The Voiceless: The Hessian doesn't speak any word in the movie. Justified for the majority of the movie which he spends without a head, but even when he gets his head back, all he utters is a growl sounding like "YAAAARRRRGGH."
    • Ichabod's memories of what happened to his mother play out without her (or Ichabod's father) uttering a single word.
  • Weapon Tombstone: The Hessian's sword marked where his body was dumped before the Tree of the Dead grew up around the spot.
  • Weapon Twirling: The Horseman has a habit of spinning his weapons during battles. To be expected, given his actor.
  • Wham Line:
    • Setting up the final act of the film: "When this cut was made, this woman was already dead!"
    • Then the following line as Lady Van Tassel steps out of the shadows, frightening Katrina.
    Lady Van Tassel: Dear stepdaughter, you look as if you'd seen a ghost.
  • What Ever Happened To The Mouse: Crane is sent to Sleepy Hollow partially to pit his newfangled scientific methods of crime fighting against an apparently supernatural threat. Did he report to his superiors that the Horseman actually was a ghost, sicced on the town by a witch in league with Satan? How was that received? We'll never know, as the plot line is dropped halfway through the film and never referred to again.
  • Who Is Driving?: Used in the opening when Peter Van Garrett is being driven at night. The Horseman kills his carriage driver, leaving it out of control before Van Garrett jumps off.
  • Wicked Witch: Subverted with the Witch of the Western Woods, who looks wicked but just wants to help. Her sister, Lady Van Tassel, plays it straight.
  • Would Hit a Girl: During the final battle, Ichabod body-tackles Lady Van Tassel off her horse and Young Masbath smacks her over the head with a heavy tree branch!
  • Would Hurt a Child:
    • The Hessian is sent by Lady Van Tassel to murder Beth Killian, the town midwife, and her family. He kills Mr. Killian right away and Beth hides her young son Thomas under the floor to protect him. She's killed next. The Hessian seems about ready to walk away...before stopping, turning back, and then stabbing his sword into the floor. The next scene shows him dropping something into his sack as he leaves the house.
    • One scene involves an autopsy of one of the victims, the Widow Winship. When examining her abdomen, Ichabod notices a strange stab wound. It turns out the Hessian also beheaded her fetus.
    • Subverted in the Horseman's past life. He simply shushed two girls to cover his position instead of simply killing them. Though it is also possible he planned on killing them, but didn't want to risk them alerting the soldiers if they screamed, given even a twig snap was enough to alert them.
  • You Can't Kill What's Already Dead: Lampshaded by Ichabod during the film's climax, when Young Masbeth asks if he's succeeded in killing the Headless Horseman.
    Ichabod: That's the problem: he was dead to begin with.
  • You Have to Believe Me!:
    • Inverted. Having seen the Headless Horseman with his own eyes, a panic-stricken Ichabod states this line several times to Baltus, Katrina, and Young Masbath. The catch is that they believe him perfectly well.
    • Played straight later in the film; after Brom's death, Ichabod insists that, despite the supernatural nature of the Horseman, he has proof that the Horseman is not simply acting out of malevolence and that there is a very real human culprit operating behind the scenes and manipulating him. However, since he's been injured and is feverish, he's brushed off.
  • You Killed My Father: Young Masbath's father, Jonathan, is the fifth victim. He readily joins Ichabod in trying to find out who's causing the deaths and helps to thwart Lady Van Tassel and thus avenge his father's murder.
  • Younger than They Look: Lady Van Tassel must be in her late twenties or early thirties, since she couldn't have been more than nine or ten when the Hessian died (Miranda Richardson was 41).


Video Example(s):

Alternative Title(s): Sleepy Hollow


Lady Van Tassel

Lady Van Tassel's fate with the Hessian at the end of the movie.

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Main / DraggedOffToHell

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