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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 village 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).

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This movie provides examples of:

  • Actor Allusion:
  • Adaptational Attractiveness: Irving describes Ichabod as a very lanky, long-nosed, odd-looking man in the story, but here in the movie, he looks like 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, and died of a random cannonball tearing his head off. The film's version had 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 undeath, he spends most of his time in the film acting as a near-unstoppable One-Man Army.
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    • Brom Bones was a pretty powerfully-built man in the original story, but he never fought anybody on-screen. In this film, he manages a pretty impressive Last Stand against the Horseman with Ichabod's (temporal) help, and would probably have won if not for the whole "undead Implacable Man" thing.
    • Ichabod himself becomes much braver and more heroic than the cowardly twerp that he was in the original story as a constable who is determined to get at the heart of a very grisly murder mystery.
  • Adaptation Expansion: This movie gives the original short story more characterization and a more involved plot. Brom Bones, originally the love rival of Ichabod Crane in the story (and 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.
  • Adaptational Heroism: The original story's Ichabod Crane was a full-blown Dirty Coward that happens to be a Gold Digger and while his final fate is left pretty ambiguous, it's harder to dispute that he didn't deserved it. This version (even if quite foppish) is a Cowardly Lion and a determined man of 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.
  • Adaptation Inspiration: As one would expect of a collaboration between Tim Burton and Johnny Depp, this is quite the quirky tale.
  • 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 Crane is originally unconvinced of the supernatural elements surrounding the murders. That is until the Magistrate is decapitated right in front of him.
  • An Arm and a Leg: The Hessian cuts off an American soldier's arm during his Last Stand.
  • An Axe to Grind: The Hessian/Horseman uses an axe as a secondary weapon.
  • 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).
  • 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.
  • Best Served Cold: Lady Van Tassel had been planning 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 Detective Ichabod Crane 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 Mary 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 succesfully 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.
  • 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 Hilarious: Tim Burton actually tried to find as many excuses as possible to have Ichabod sprayed in the face with blood. Later becomes an example of Not Funny Anymore, 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.
  • Catapult Nightmare: Ichabod. A lot.
  • 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 realise 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.
  • Children Are Innocent: Averted with Lady Van Tassel when she was a little girl and apparently cruel from the start.
  • Cool Horse: Next up on Pimp My Horse, we examine the Hessian's ride, Daredevil.
  • Cool Sword: The Horseman has a totally sick black 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 handwaves 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.
  • 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 is murdered by the Horseman before the film even reaches two minutes.
  • Dead to Begin With: Ichabod and 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.
    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 of a Child: Tim Burton says in the DVD commentary that he dislikes it when children are always spared from danger in horror films.
    • One victim is beheaded whilst in its mother's womb.
    • A young boy is dragged out of the cellar by the Horseman and then beheaded.
  • 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.
  • Devil, but No God: All supernatural elements are the work of occult magic. Even when the Horseman finds that he can't enter the church, it's because Katrina has drawn a sigil inside.
  • 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 rides 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 her stepdaughter Katrina.
  • Everything's Better with Spinning:
    • The Horseman has a habit of spinning his weapons during battles. To be expected, given his actor.
    • 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 flashbacks.
  • Expository Hairstyle Change: After she's revealed to be evil, Lady Van Tassel's hair is loose, while before she always wore it up.
  • 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.
  • 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.
  • 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 mercenary/Headless Horseman worked for the English 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.
    • 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.
  • 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 had her mother (a witch) executed, leaving her and her twin sister completely destitute and forced to live in the woods.
  • 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.
  • 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: A former mercenary who died by decapitation is 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 and dragging her to Hell.
  • He Knows Too Much:
    • Masbath the Elder 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).
  • 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.
  • 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 that way 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, which spears Baltus, drags him to the fence, and then decapitates him.
    • The fate of Ichabod's mother, in an Iron Maiden.
  • Imperiled in Pregnancy: One of the Horseman's victims is a pregnant woman. The Horseman beheads both the woman and the baby.
  • Impoverished Patrician: Lady Van Tassel's family was forced into this by Van Garret, 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.
  • 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.
  • 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 that 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.
  • In Name Only: In Irving's story, Ichabod Crane was a schoolteacher who fully believed in ghosts, and the Headless Horseman never went on a killing spree.
  • Iron Maiden: Ichabod Crane remembers that his mother was locked in 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.
  • I Owe You My Life: Presumably the reason why the Horseman doesn't go for Katrina.
  • 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 accuses her of controlling the Horseman. In the end, though, she turns out to be good after all.
      Ichabod: Villainy wears many masks, none of which so dangerous as the mask of virtue.
  • 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, impale his next victim and drag him out that way before beheading him.
  • Lovecraft Country: The town of Sleepy Hollow and surrounding spooky woods comprise a spiritual cousin, at least.
  • The Man Behind the Man: Lady Van Tassel is the one really 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 and his wife and young son is 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.
  • 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.
  • Noble Demon: The Horseman, both in his past life and his ghost life.
  • Nothing Is Scarier: Lampshaded in the woods.
  • 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.
  • 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-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.
  • 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.
  • 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.
  • Oh, Crap!: Lady van Tassel gives a particularly great one when she realizes in whose arms she just woke up after the final showdown.
  • Off with His Head!: The Headless Horsman's favorite way to kill people is to cut their head off with his sword, both when he was alive and a mercenary and now that he's a ghost.
  • Ominous Fog: Rolls in and puts out the torches before the Horseman comes riding in.
  • Papa Wolf: Mr. Killian tries to fight the Horseman to save his family, but the Horseman kills him before going after his wife and child.
  • Pet the Dog:
    • The Headless Horseman clearly adores his horse. 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: This 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.
  • 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 practises 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 pre-headless Horseman once 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 this time, unlike in his previous life, he feels no pleasure in killings. Moreover you can see that when he has killed his specific targets, he simply heads back in the forest, not caring of no one. Even when Brom attacks him, he simply overpowers him and begins to leave, showing that he is not interested in killing. Unfortunately, Brom was too brash for his own good and so he ended 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.
  • 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 also 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...
  • 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 the horse of the Headless one 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.
  • 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 beats Dr. Lancaster to death for saying too much to Baltus.
    • Ichabod's dad, who hated witches and figured the only way to save his wife's soul is 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.
  • Skepticism Failure: Crane 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.
  • Snow Means Death: It was snowing when the Hessian became the Headless Horseman.
  • 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 children 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 the 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 realises 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.
  • 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.
  • The Three Faces of Eve: The three prominent female characters. Katrina, as the youngest, is of course 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 had a fling with the reverand.
  • 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.
  • Unwitting Pawn: The Horseman himself. Lady Van Tassel uses him to kill people for her personal reasons.
  • The Vamp: Lady Van Tassel, who manages to seduce Reverend Steenwyck into her service.
  • 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.
  • Wham Line: Setting up the final act of the film: "When this cut was made, this woman was already dead!"
  • Wicked Witch: Subverted with the Witch of the Western Woods, who looks like wicked but just wants to help. Her sister plays it straight.
  • Would Hit a Girl: Both Ichabod and Young Masbath fall into this trope, Ichabod by body-tackling Lady Van Tassel off her horse and Young Masbath by smacking her over the head with a heavy tree branch!
  • Would Hurt a Child:
    • The Hessian is sent by Lady Van Tassel to murder the midwife of the town and her family. He kills the father right away and the midwife hides her young son 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 female victims. When examining her abdomen, they notice 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 Crane during the film's climax, when his young ward, Masbeth, asks if he's succeeded in killing the Headless Horseman.
    [the group watches as the Horseman steps out of the burning windmill, unscathed]
    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 the town elders. The catch is that they believe him perfectly well; it's been them who have been trying to convince him of the Horseman's existence since the beginning of the film.
    • 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, was the fifth victim. Masbeth readily joins Ichabod in trying to find out who's causing the deaths, and helps to thwart Lady Van Tassel and 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 forty-one.
  • Your Cheating Heart: Lady Van Tassel is married to Baltus, but has no qualms having sex with the town reverend, out in the woods where they can easily be seen. Later it becomes clear that she never even loved her husband to begin with, and her affair was probably part of her plan to get revenge on the Van Tassels.
    • Dr. Lancaster, though already in a long, stable and possibly loveless marriage, is secretly engaging in an passionate affair with the younger more attractive servant girl Sarah as briefly witnessed by Icabod Crane upon his arrival in Sleepy Hollow and again later in a flashback told by Lady Van Tassel who blackmailed him for his complicity in exchange for her silence on his fornications with his younger mistress.

Alternative Title(s): Sleepy Hollow

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