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File:Sleepy Hollow 1999.jpg
Heads will roll.
A poster advertising the film.

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 and Christopher Walken.

The story centers on police constable Ichabod Crane 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.

This Movie Contains Examples Of:

  • Adaptational Attractiveness: The original description of Ichabod Crane sounded nothing like Johnny Depp.
    • Almost averted. Johnny Depp originally wanted the full makeup to look quite unattractive, but the producers advised him to be himself.
  • Adaptation Expansion: This movie gives the original short story more characterization and a more involved plot.
    • Not only that, but 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 and perishes in single combat against the Horseman.
  • Agent Scully: Ichabod Crane is this at the beginning of the investigation until the supernatural nature of the crimes becomes obvious.
  • Anti-Villain: Arguably the Horseman. Although he is behind the many decapitations occurring in the town, he is under the control of the true villain, and thus, is just doing the bidding until Ichabod is able to have him regain his head and rightful mind.
    • Although, that said, the reason why he was killed in the first place was because he was a Blood Knight Omnicidal Maniac. There is a very good reason that every time he rides out, he comes from the depths of Hell!
  • Ax Crazy: Lady Von Tassell. At one point with a literal axe!
    • The Headless Horseman also has an axe and knows how to use it.
  • Best Served Cold: The Big Bad had been planning revenge since childhood.
  • Better to Die Than Be Killed: Notary Hardenbrook commits suicide by hanging rather because he expects to be the Horseman's next victim.
  • Bitch in Sheep's Clothing: Lady Van Tassel
  • Black Comedy: perhaps one of the few film to ever qualify as a black action-comedy
  • Bloodier and Gorier: Damn skippy.
  • Bloody Hilarious: Tim Burton actually tried to find as many excuses as possible to have Ichabod Crane sprayed in the face with blood.
  • Blood Knight: The Hessian.
  • Catapult Nightmare: Ichabod. A lot.
  • Children Are Innocent: Maybe that's another main reason why the Hessian spared the little girl's life simply sushed'em.
  • Cool Horse: Next up on Pimp My Horse, we examine the Hessian's ride, Daredevil, as an example of Doing It Right.
  • Cow Tools: The autopsy sequence.
  • Cute Witch: Katrina, maybe a bit older than your average cute witch, but cute anyway
  • 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 children 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.
  • Dead to Begin With: The problem of asking, "Is he dead?"
  • Death by Adaptation: Brom
  • Deliberately Monochrome: All the colours are dulled except for the blood.
  • Dragged Off to Hell: Lady van Tassel's fate with the Hessian.
  • Dual-Wielding: Used by the Hessian, to great effect, and Brom, not so much.
  • Eagle-Eye Detection: Ichabod's preferred method for solving the streak of murders.
  • Enforced Method Acting: According to the director's commentary on the DVD, during the scene in the church where the doctor is killed by a blow to the head, they accidentally hit Ian McDiarmid so hard that he ended up having to go to hospital.
  • Everything's Better With Spinning: The Horseman has a habit of spinning his weapons during battles.
    • It's also mentioned somewhere on the DVD (maybe the 'making of') 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.
  • Fainting: Ichabod. A lot. Though he does manage to hold out until the scary thing is over.
  • Fake Brit: Johnny Depp as Crane, though to be fair he's from New York in 1799.
    • Technically, every major character in the movie with the exception of the Hessian Horseman would have been born a Brit(if you date the foundation of the US to the Treaty of Paris in 1783)
  • Fascinating Eyebrow: Ichabod's initial reaction to anything intriguing or unusual.
  • Fate Worse Than Death: Lady Von Tassel was still alive when the Horseman went back to the Hollow. He presumably has...plans...for her.
  • Fan Service: Burton's arm candy girlfriend at the time, Lisa Marie, shows up in some dream sequences.
    • As Ichabod's gorgeous mother. The script actually called for a scene for her to dance while loosening her top, until she was pretty much topless.
      • Ichabod himself counts as this.
  • Flaming Sword: Not actually in flames, but it 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.
  • Half the Man He Used To Be: Brom
  • Headless Horseman
  • Hell Gate: The Tree of the Dead is where the Horseman travels between Earth and the underworld.
  • Hellish Horse: Daredevil.
  • Heroic BSOD: Twice.
  • Hoist by His Own Petard: How the Hessian Horseman was killed...originally...
  • Horror Struck: Ichabod, after seeing the Horseman up-close for the first time.
  • Hot Mom: Ichbod's mom.
    • Lady Van Tassel is a Hot Stepmother.
    • The midwife Elizabeth Killian ain't that half-bad either.
  • Hot Witch: Ichabod's mom, although her status as a witch is debatable. Also Lady Von Tassel can be considered an evil example since she doesn't fit the Vain Sorceress trope
    • It's pretty much proven that Katrina is a witch (or just practices witchcraft), since she was seen making a potion and chanting a spell when Icabod fell ill.
  • Impaled with Extreme Prejudice: Baltus van Tassal
  • Infant Immortality: Averted twice. One victim was beheaded whilst in its mother's womb.
  • In Name Only: Pretty much. In the Irving's story, Ichabod Crane was a school teacher who fully believed in ghosts, and the headless horseman never went on a killing spree.
  • Innocent Bystander: Ichabod survives many encounters with the Horseman on account of this. The Horseman is shown to ignore anyone who doesn't directly interfere with his taking heads or doesn't get in his way. Not that Brom listened...
  • It's Going Down: The windmill. Monster movies hate windmills.
  • 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.
  • Kid Detective: Ichabod is described by Tim Burton as a thirteen-year-old girl-detective in a man's body.
  • Killed Mid-Sentence: Doctor Lancaster
  • Large Ham: Miranda Richardson cheerfully NOMS down any scenery that isn't nailed down or on fire after The Reveal.
  • Last Grasp At Life: How Lady van Tassel's hand appears in the Tree of the Dead when the Hessian drags her to hell.
  • Light Is Not Good: Ichabod's father's eye-searingly white church hides a dungeon filled with torture devices.
    • Played with with Katrina. As she the only character to dress in light colors and ride a white horse, her significance is clear immidiately to a Genre Savvy viewer. When combined with her witchcraft, this makes her legitimately suspcious by the time Ichabod accuses her of controlling the horseman. In the end, though, she turns out to be a good guy after all.

  Ichabod: Villainy wears many masks, none of which so dangerous as 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.
  • Lovable Coward: Ichabod. Even after he toughens up a bit toward the end, he is still in the habit of using women and children as Human Shields.
  • Lovecraft Country: The town of Sleepy Hollow and surrounding spooky woods comprise a spiritual cousin, at least.
  • 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.

  • Mr. Exposition: When the true villain is finally revealed, she goes into a long, long Info Dump of raw, untreated exposition that details her entire scheme in agonizing detail.
  • Mythology Gag: Brom's fake Horseman prank closely mirrors Ichabod's encounter with the horseman in The Legend of Sleepy Hollow.
  • Noble Demon: The Horseman.
  • Nothing Is Scarier: Lampshaded in the woods.
  • Non-Action Guy: Ichabod.
  • Oedipus Complex: Ichabod falls like a brick for the cute witch Katrina van Tassel. His mother was "an innocent child of nature" "condemned, murdered to save her soul" by his father - a "Bible-black tyrant 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 witch for her compassion.
  • Off with His Head: The Movie.
  • Ominous Fog: Rolls in and puts out the torches before the Horseman comes riding in.
  • One-Scene Wonder: Christopher Walken plays a pre-headless horseman, and has no lines other than "Shhh" and "Raaa!!", yet there are many people who consider it to be his greatest performance ever.
    • Also Christopher Lee, who shows up in one scene at the beginning as the magistrate who orders Crane to investigate the killings at Sleepy Hollow.
  • Only Sane Man: Ichabod thinks he's this.
  • 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.
    • When he encounters two girls in the woods, he tries to shush them to prevent them from giving away his position, when he probably would have had an easier time of it by simply killing them.
  • Pimped-Out Dress: Since this isn't a poor town.
  • Pocket Protector: Ichabod is saved from a shot to the chest by Katrina's book.
  • Protective Charm: Katrina's pentagram.
  • Psycho for Hire: The pre-headless Horseman once worked for the Redcoats, not for money but for the love of killing.
  • 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 the audience that he is not interested in killing. Unfortunately Brom was too brash for his own good and so he ended cleaved in twain.
  • Reality Ensues: Katrina's father manages to get to the church, whose property the Horseman can't enter. He thinks he's safe. Then the Horseman snaps off a fencepost, ties it to a rope, throws it through the window like a spear, and drags him out of the church.
  • Scary Scarecrows
  • Screams Like a Little Girl: Oddly averted; Ichabod does everything like a little girl except scream.
    • He still manages to work in a handful of girly whimpers and gasps here and there.
  • Seeking Sanctuary: 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 recognise it immediately from one of his 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 Ichabod suddenly realizing he's on the horse of the Headless one.
      • The fact that Brom disguises himself as the Horseman to freak out Ichabod would count as well.
      • Also, the wooden bridge which the Headless Horseman can't cross in the story ... serves as a Hope Spot in this particular version.
    • Come to think of it, the dress Katrina wears at the end is the same material as the Beetlejuice tuxedo.
  • Sinister Minister: The Reverend 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; Ichabod's dad hates witches and figures 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.
  • 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.
  • Stunt Casting: Look out for Martin Landau and Christopher Lee early in the film.
  • Torture Cellar: Ichabod's father killed his free-spirited wife in one of these by locking her in an iron maiden.
  • Troubled Backstory Flashback: The fate of Ichabod's mother.
  • Unholy Matrimony: Played for horror (yeah, the irony) 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. Lovely.
  • The Vamp: Lady Van Tassel
  • The Voiceless: The Hessian unless we should count: YAAAARRRRGGH.
  • Wicked Stepmother: Lady Van Tassel
  • Wicked Witch: Subverted with the Witch of the Western Woods, who looks like wicked but just wants to help.
  • 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 stabbing his sword into the floor. The next scene shows him dropping something into his sack as he leaves the house.
    • An earlier 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.
  • You Look Like You've Seen a Ghost: For very good reason, too...