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Film: Sleepy Hollow
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 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.

This Movie Contains Examples Of:

  • Adaptational Attractiveness: The original description of Ichabod Crane sounded nothing like Johnny Depp. He 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. 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.
  • Adaptation Inspiration: As one would expect of a collaboration between Tim Burton and Johnny Depp, this is quite the quirky tale.
  • Agent Scully: Ichabod at the beginning of the investigation until the supernatural nature of the crimes becomes obvious.
    Ichabod: But it was a Headless Horseman!
    Baltus: Of course it was; that's why you're here.
  • Ax-Crazy:
    • Lady Van Tassel. At one point with a literal ax!
    • The Headless Horseman has an ax and knows how to use it.
  • Badass: The Horseman.
  • Best Served Cold: Lady Van Tassel 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 films to ever qualify as a black action-comedy.
  • Blondes are Evil: Lady Van Tassel.
  • Bloodier and Gorier: Damn skippy.
  • 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.
  • Catapult Nightmare: Ichabod. A lot.
  • 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.
  • Children Are Innocent: Maybe that's another main reason why the Hessian spared the little girl's life simply shushed them.
  • Creepy Child: Lady Van Tassel, as the above little girl.
  • Cool Horse: Next up on Pimp My Horse, we examine the Hessian's ride, Daredevil, as an example of Doing It Right.
  • Cowardly Lion: Ichabod
  • Cow Tools: The autopsy sequence.
  • Cranium Chase: The Headless Horseman.
  • Cute Witch: Katrina, who's 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 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.
  • Dark Magical Girl: Katrina has strong whiffs of this trope as well, what with her enigmatic yet kind presence.
  • Dead to Begin With: The problem of asking, "Is he dead?"
  • Death by Adaptation: Brom. Considering that the movie bears little-to-no resemblance to the book, this is hardly that surprising.
  • Deliberately Monochrome: All the colors are dulled except for the blood.
  • Demotedto 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.
  • Doing in the Wizard : Played with; Ichabod is initially determined to do this, convinced that the Horseman is just an old ghost story, only to learn that he is very real. However, contrary to the credulous panicking of the town elders, who are convinced it's just acting out of pure malevolence, Ichabod is entirely correct that there is a very human nemesis operating behind everything.
  • Dragged Off to Hell: Lady Van Tassel's fate with the Hessian at the end of the movie.
  • Dual Wielding: Used by the Hessian, to great effect. Brom, not so much.
  • 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, 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.
    • 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.
  • Fainting:
    • Ichabod. A lot. Though he does manage to hold out until the scary thing is over.
    • Katrina faints first when her father is killed right before her eyes and secondly when her stepmother, whom she thought was killed by the Horseman, enters the house to greet her.
  • Fascinating Eyebrow: Ichabod's initial reaction to anything intriguing or unusual.
  • Fate Worse than Death: Lady Van Tassel was still alive when the Horseman went back into the Tree of the Dead. He presumably has...plans...for her.
  • Fanservice: 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 where she dances while loosening her top until she's pretty much topless.
  • 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.
  • 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.
  • Hellgate: The Tree of the Dead is where the Horseman travels between Earth and the underworld.
  • Heel-Face Turn: The Horseman, arguably at the end. Once he gets back his head, he gives the 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.
  • Heroic BSOD: Happens to Ichabod 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 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 fell ill. She goes more for a mix of Cute Witch and Dark Magical Girl.
  • Human Shield: Ichabod has a tendency to subtly position other people to stand in front him during moments of danger and crisis.
  • Impaled with Extreme Prejudice: Baltus Van Tassel during the church attack.
  • Imperiled in Pregnancy: One of the Horseman's victims is a pregnant woman. The Horseman beheads both woman and 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.
  • Infant Immortality: Averted twice. One victim was beheaded whilst in its mother's womb.
  • 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. Not once.
  • The Ingenue: Katrina, despite Christina Ricci being mostly known for playing dark-haired creepy kids and vamps.
  • 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.
  • 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. 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.
  • Kid Detective: Ichabod is described by Tim Burton as a thirteen-year-old girl-detective in a man's body.
  • Killed Mid-Sentence: Dr. Lancaster, by Reverend Steenwyck.
  • Large Ham:
  • 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 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.
  • 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.
    • 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, Lady Van Tassel, 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.
  • Nice Job Fixing It, Villain: 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 body of the servant girl that 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, Sarah was already dead.
  • Noble Demon: The Horseman, both in his past life and his ghost life.
  • Nothing Is Scarier: Lampshaded in the woods.
  • Non-Action Guy: Ichabod. He then later becomes an Action Survivor.
  • 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.
  • 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 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.
  • Ominous Fog: Rolls in and puts out the torches before the Horseman comes riding in.
  • 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. Considering that the sound of a snapping twig was enough to alert the enemy soldiers, it's unlikely that killing the children was an option for staying inconspicuous.
  • Pimped Out Cape: Katrina greets Ichabod in the Western Woods while wearing a long hooded white velvet cape.
  • 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 still wear fur-trimmed dresses in the winter.
  • Pocket Protector: Ichabod is saved from a shot to the chest by Katrina's book.
  • 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.
  • 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 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 fence post, ties it to a rope, throws it through the window like a spear, and drags him out of the church.
  • Red Herring: There are clues pointing to both Baltus and Katrina as the culprit before Ichabod finally twigs upon the truth.
  • Scary Scarecrows: Plenty of them all throughout Sleepy Hollow, but most notably the familiar pumpkin-headed scarecrow at the very beginning of the film.
  • Screams Like a Little Girl: Ichabod does everything like a little girl except scream. He 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 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 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.
  • 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.
    • 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.
  • 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.
  • 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.
  • Unwitting Pawn: The Horseman himself. Lady Van Tassel used 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 unless we should count: YAAAARRRRGGH.
  • Wicked Stepmother: Lady Van Tassel to Katrina.
  • 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 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 prevent 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 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, his claims are dismissed as delusional rantings.
  • You Killed My Father: Young Masbath's father, Jonathan, was the fifth victim.
  • You Look Like You've Seen a Ghost: For very good reason, too...

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