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    Ichabod Crane 

https://static.tvtropes.org/pmwiki/pub/images/ichabod_300.jpg

Played by: Johnny Depp, Sam Fior (as a child)

The protagonist of the movie, a police constable sent to Sleepy Hollow from New York City to investigate a series of murders.


  • Action Survivor: By the end of the movie, he has survived the Horseman's attacks on Sleepy Hollow.
  • Adaptational Attractiveness: The original description of Ichabod Crane was nothing like the good-looking Johnny Depp. Depp wanted the full makeup to look quite unattractive, but this ultimately did not happen.
  • Adaptational Badass: In the original, all he did was court a woman and get chased by a guy with a pumpkin as a head, doing nothing to defend himself. Here, he holds off both the indestructible Horseman and the Big Bad herself.
  • Adaptational Heroism: His short story counterpart was nothing more than a selfish, greedy ladies' man. This time around, he's a police constable fighting off a Serial Killer.
  • Agent Scully: As a policeman, he firmly believes that everything has a rational explanation and he believes in science over the supernatural. However, over the course of the film, he just simply can't deny the obvious supernatural nature of the crimes anymore.
  • Catapult Nightmare: He does this a lot over the course of the movie.
  • Cowardly Lion: For the most part, he tends to pass out whenever anything creepy happens. Until the end at least, when he manages to hold out until the Horseman takes Lady Van Tassel back to Hell with him before fainting.
  • Dark Is Not Evil: Despite being an Eerie Pale-Skinned Brunette (and wearing dark clothes in most of his scenes), he's absolutely not a villain.
  • Doing In the Wizard: Played with; he comes to the town believing the Headless Horseman to only be the work of a madman, but soon finds out just how real the Horseman is.
  • Eerie Pale-Skinned Brunette: Pretty much how Depp is played in most Tim Burton films; he has very white skin and dark hair.
  • Fainting: He faints many times throughout the film, mostly when seeing bloody corpses, and notably when he first sees the Headless Horseman.
  • Fascinating Eyebrow: His most common reaction to most anything interesting.
  • Hollywood Atheist: Lost his faith in childhood when he found out that his father tortured and murdered his mother for being a witch.
  • Human Shield: Ichabod has a tendency to subtly position other people to stand in front him during moments of danger and crisis.
  • Innocent Bystander: He is present at, but survives, a few of the Horseman's attacks. This is because the Horseman doesn't go after anyone but the intended target as long as said bystander doesn't attempt to interfere.
  • Lovable Coward: He quivers with fear when he first sees the Headless Horseman, has a tendency to run away from any dangerous situation, and many times faints out of fear; this is played as him being Adorkable. He does become braver towards the end, though.
  • Muggle–Mage Romance: He ends up falling for Katrina.
    • He also was born from one of these. Since his father was quite the religious zealot, it didn't end well for his mother.
  • Only Sane Man: He at first believes he is the only sane person in Sleepy Hollow because he believes in science and a rational explanation for the murders, instead of the townspeople, who believe in ghosts and magic. He then gets dragged into the madness along with the rest of the town, but he is the one who realizes that the Horseman isn't acting of his own accord but is controlled into doing his actions by a living human.
  • Pocket Protector: He's saved from a gunshot wound by Katrina's book, which he carries inside his jacket.
  • Right for the Wrong Reasons: Ichabod at first believes the Hessian is nothing more than a Serial Killer of flesh and blood and actually has a motive for the murders. Turns out the Horseman isn't still a human, but he's entirely right that some human has a motive...
  • Science Hero: The reason he's sent to investigate the events in Sleepy Hollow in the first place is to prove to the New York police that there is something of use in that newfangled "forensic science" that he's constantly talking about. As well, said forensic science (performed with gadgets of his own design) provide various clues and firm proof that the killer is supernatural (although it takes longer for him to accept it...).
  • Screams Like a Little Girl: Actually not played straight at all, surprisingly, given his Cowardly Lion nature. He does let out some womanly shrieks, though.
  • Would Hit a Girl: He tackles Lady Van Tassel off her horse and starts wrestling her for the Horseman's head.
  • You Have to Believe Me!: Inverted. Right after Ichabod witnesses Magistrate Philipse being beheaded right in front of him, he freaks out and says this to Baltus. Baltus believes him, of course, but up until then, he and the town elders had been the ones trying to convince him of the Horseman's existence instead of the other way around.
    Ichabod: But it was a Headless Horseman!
    Baltus: Of course it was; that's why you're here.
    Ichabod: No, no, no, you have to believe me; it was a Headless Horseman!

    Katrina Van Tassel 

https://static.tvtropes.org/pmwiki/pub/images/katrina_300.jpg

Played by: Christina Ricci

  • Action Girl: She has moments at the end when she's this, but it's generally downplayed so much that she's really just an Action Survivor.
  • Fainting: Twice. First when her father is impaled by the Horseman and then decapitated, then when her supposedly dead stepmother comes in and casually says hello.
  • Geometric Magic: She draws magic circles which serve as defense against evil.
  • Hair of Gold, Heart of Gold: She's a sweet-natured blonde. That pretty much sums it up.
  • Hot Witch: A pretty young woman who regularly practices benevolent magic.
  • The Ingenue: She's a sweet and kind girl. Notably, she's the only townsperson to be friendly and welcoming to Ichabod.
  • Light Is Good: She's just about the only character in the whole movie to wear colors like gold and pure white, and is easily the most kindhearted person in Sleepy Hollow.
  • Neutral Female: During the climax when Ichabod and Lady Van Tassel are fighting over the Horseman's skull, 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.
  • Missing Mum: Her mother died prior to the start of the story, since her father has since remarried.
  • Pimped-Out Cape: Katrina greets Ichabod and Young Masbath while wearing a long hooded white velvet cape with embroidered edging. She later regularly wears it in scenes taking place outside, as seen here.
  • Protective Charm: She casts a spell to protect Ichabod from harm in his guest room and later a spell to keep the Horseman out of the church where the townspeople are taking refuge from him.
  • Red Herring: Some clues point to her being the one controlling the Horseman, but she isn't.
  • Token Good Teammate: To the Van Tassels. She's the only one who didn't have anything to with her stepmother's land being seized.
  • Wicked Stepmother: She doesn't get along with the wife her father took after her mother died. Her stepmother turns out to be truly wicked, as she killed many townspeople by using the Horseman (worse than a normal murder, as that means their souls would go to Hell) and even tries to make Katrina herself suffer that fate.
  • You Look Like You've Seen a Ghost: Lady Van Tassel tells Katrina this when she walks in the room after the whole town believed her to be dead.
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    Headless Horseman 

Played by: Christopher Walken, Ray Park (headless)

https://static.tvtropes.org/pmwiki/pub/images/thehessian.jpg

  • Alas, Poor Villain: Despite his murderous appetites, it's kinda sad to watch him go down just after he was trying to comfort his dying horse.
  • Anti-Villain: Type I. The Headless Horseman was an Ax-Crazy Blood Knight in life who lived to kill, but he has a sense of honor and a code of ethics.
  • Ax-Crazy: Oh, yes. The whole reason he joined the war effort was so he could kill, and kill and kill he does, and he clearly enjoys it, if his screams are any indication.
  • Badass Cape: That he doesn't even discard after his death.
  • Badass Normal: When he was human, he massacred soldiers by the dozens, with seemingly little effort. He becomes an Empowered Badass Normal when he comes back, being indestructible, though he's kept on a leash.
  • Blood Knight: He lives to bathe in blood.
  • Dark Is Evil: In life, he was clad in black and was a Hessian mercenary who aided the British just so he could exercise his love for violence. After death, he's a force of Hell. Ironically, he's less evil this way.
  • Determinator: Much like the Trope Namer, once he's set on a target, he absolutely will not leave them be until they're dead.
  • The Dog Bites Back: Literally. After being brought back from the dead and forced to kill people — including children — on Lady Van Tassel's behalf, he chews her lips with his sharpened teeth.
  • The Dragon: He's Lady Van Tassel's personal assassin.
  • Eerie Pale-Skinned Brunette: Had black hair and white skin in life and after getting his head back.
  • Even Evil Has Loved Ones: He was genuinely devastated when his horse Daredevil was shot. He even reunited with Daredevil with a gentle stroke after his head was restored by Crane.
  • Even Evil Has Standards:
    • While he thoroughly enjoys senseless butchery, he refuses to murder children when he can help it. For that matter, he doesn't seem particularly interested in killing anyone he doesn't have to kill.
    • He spares Ichabod, Katrina, and Young Masbath when the former returns his skull to him, and instead drags Lady Van Tassel off to Hell.
  • Genius Bruiser: As the Headless Horseman, he can't enter holy ground, but is clever enough to find a Loophole Abuse by fashioning a harpoon to catch and pull out his latest victim from the outside.
  • Hoist by His Own Petard: Flashbacks show him beheading many soldiers he came across with a sword, and he's killed with the same sword in the same way.
  • Implacable Man: Nothing can stop the Horseman; not being shot (multiple times), having a carriage dropped on him, or even being caught in an exploding windmill. As Ichabod points out, it's damn near impossible to kill someone when they're already dead.
  • Kick the Son of a Bitch: Dragging Lady Van Tassel off to Hell after she used him to carry out a string of murders — including a child — to acquire the Van Tassel estate.
  • Large Ham: He may be a man of few words, but his screams as he's chopping off heads speak volumes about him.
  • More Teeth than the Osmond Family: Filed them down to points to reflect his fearsome-ness.
  • Noble Demon: Even when he was alive, he clearly had a code of ethics. Though he joined the war effort solely because he liked to kill, it's suggested that he doesn't kill anyone without provocation, especially children. He apparently carried this over into undeath, when he appears to have every intention of letting Brom live, letting him off with a warning (read: a dagger to the leg) until Brom keeps trying to kill him.
  • No Good Deed Goes Unpunished: He stays behind when his horse gets shot, but that leaves him to be spotted by the soldiers. His refusal to kill the little girls when he runs across them also comes back to bite him. One of them, the future Lady Van Tassel, snaps a twig, giving away his position so that the soldiers can catch up to him. All so she could use him to get her revenge on the Van Garretts and the Van Tassels.
  • Off with His Head!: It's his whole MO. Needless to say, he ends up on the receiving end of this.
  • Pet the Dog:
    • A literal example, as he comforts his dying horse while showing genuine grief.
    • He spares Ichabod and Katrina after he gets his head back.
  • Punch-Clock Villain: Not as much when he was alive, where he killed For the Evulz, but after death, he becomes an Unwitting Pawn for Lady Van Tassel to exact her revenge. And once he gets his skull back, he spares the heroes.
  • Sociopathic Soldier: More like "sociopathic mercenary", but same deal. He joined the British forces not to keep the colonists under the yoke of England, but to revel in carnage.
  • Super Strength: Upon his reincarnation, he can batter down stout wooden doors with ease, throw an improvised spear hard enough to completely impale a man, and while on horseback and using only one arm, he can lift an unconscious woman off the ground and onto his saddle with no apparent effort.
  • Taking You with Me: After being given his skull back, he reunites with his horse and they travel back to Hell, taking Lady Van Tassel with them to make them pay for her crimes and fulfill her side of the deal with the Devil.
  • Wouldn't Hurt a Child: When he was alive, he ran across a couple of little girls in the woods when he was hiding from a band of American soldiers. Rather than threatening or killing them, all he did was shush them quietly. This completely goes out the window upon his resurrection, when he murdered the widow Emily Winship's unborn child and the young boy Thomas Killian, although he only did so because he was under the command of Lady Van Tassel.

    Lady Van Tassel 

Played by: Miranda Richardson, Tessa Allen-Ridge (as a child)

https://static.tvtropes.org/pmwiki/pub/images/82676a71d6d47d8011baa313fea81924_400x400.jpg

  • Asshole Victim: Given the number of people she had killed by the Horseman, several that weren't responsible for the ruining of her family, it's hard to feel sorry for her when the Horseman drags her to hell.
  • Ax-Crazy: Aside from using a literal axe on two of her victims (one of which was her sister), she becomes a lot more openly unhinged once she reveals her true colors.
  • Big Bad: It's her lust for revenge that drives the Horseman to kill for her.
  • Bitch in Sheep's Clothing: She is hospitable to Ichabod for most of the movie and appears to mourn the death of Notary Hardenbrook, but she is actually responsible for nearly everything that's gone wrong.
  • Cain and Abel: The Cain to her sister's Abel. She uses her magic for revenge, even killing people who had nothing to do with her losing her home because they were in her way or knew too much.
  • Deal with the Devil: She claims to have made one to ensure her vengeance on the Van Garretts and the Van Tassels.
  • Evil Counterpart: To her sister, the unnamed crone. Both of them practice dark magic, but while her sister is content to be left alone in the woods only to be sought out when her aid is needed, Lady Van Tassel is quite a lot more ambitious and petty, to the point where she murders her sister.
  • Evil Is Petty: She'll kill anyone to fulfill her revenge, even children, and murders her own sister just for helping Ichabod.
  • Evil Wears Black: Once she reveals her true colors to Katrina, she's wearing a black dress.
  • Freudian Excuse: The Van Tassels and the Van Garretts seized her family's land and left her and her sister without a home, so she's actually not entirely wrong to be so angry. However, it doesn't justify murdering her own sister, or the servant girl out of pure spite, or the midwife who knew Widow Winship had been pregnant, nor does it excuse her greed, which makes her just as bad as the families she was seeking revenge against, and probably even worse.
  • Hot Witch: Of the evil variety.
  • Kick the Dog: Senselessly ordering the Horseman to murder the child Thomas Killian is one to both to the child and to the Horseman, who refused to kill children when he was alive. It makes her comeuppance at his hands that much more satisfying.
  • Lady of Black Magic: She is quite an attractive woman, who acquired her power to control the Horseman through a Deal with the Devil in childhood and married into the Van Tassel family with the intent of murdering them all and acquiring their wealth.
  • Non-Action Big Bad: Subverted. It looks like the Horseman does most of the dirty work for her, but she admits to poisoning Katrina's mother, along with beheading her own sister and Sarah the servant girl.
  • Walking Spoiler: The fact that her entire folder is spoiler-tagged is more than enough information here, but it is very difficult to talk about her role in the film without mentioning her connections to the Horseman.
  • Wicked Stepmother: She poisoned the original Lady Van Tassel and married into the family to exact her revenge from within.
  • Would Hurt a Child: Unlike the Horseman, she has no qualms in either hurting or killing children to complete her goal, as she ordered the Horseman to kill Emily Winship's unborn child and the young Thomas Killian, and later tried to do the same to her stepdaughter Katrina.

    The Crone 

https://static.tvtropes.org/pmwiki/pub/images/maxresdefault_1_141.jpg

Played by: Miranda Richardson, Cassandra Farndale (as a child)

  • Cain and Abel: The Abel to her sister, Lady Van Tassel. Unlike her sister, she doesn't show any interest in hurting anyone for her magic, though she does kill a bat.
  • Creepy Good: "Good" might be a bit of a stretch, since we don't know much about her and she does commune with demonic forces, but as eccentric as she is, she doesn't seem to use her magic for malicious purposes. And she's certainly a lot less evil than her sister.
  • Dark Is Not Evil: She's implied to be a devil-worshiper and isn't above animal sacrifice, not to mention her face when the "other" (implied to be a demon or possibly even Satan himself) possesses her is utterly horrifying, but her only purpose to help Ichabod find the Horseman. Also, she restrains herself in chains to make sure she can't hurt Ichabod while she summons the aforementioned "other."
  • Demonic Possession: A voluntary and temporary sort, accomplished by the burning of incense and spilling the blood of a bat.
  • Nightmare Face: Does the picture not say enough for you? In the movie, it manages to be even worse, with her eyes and tongue stretching to impossible lengths and popping out of her head. Notably, though, her real face is actually quite attractive.
  • Off with Her Head!: Killed by her sister this way.
  • The Ophelia: She's definitely more than a little crazy, and when we get to see her real face in a flashback, she's surprisingly beautiful.
  • Solitary Sorceress: Lives out in the Western Woods by herself and practices spells.

    Brom Van Brunt 

https://static.tvtropes.org/pmwiki/pub/images/brom_van_brunt.png

Played by: Casper van Dien

  • Badass Normal: A skilled marksman and hand-to-hand fighter.
  • Death by Adaptation: While in the original story he makes out much better than Ichabod, here he's got one of the most violent and gory of the deaths.
  • Death by Irony: He dresses up as the Horseman to scare Ichabod, only to fall prey to the real Horseman's blades later.
  • Demoted to Extra: In Washington Irving's short story, he's Ichabod's rival and the one Katrina chooses over him. Here, his role is considerably toned down.
  • Green-Eyed Monster: Takes against Ichabod right away because Katrina kisses him as part of a party game.
  • Half the Man He Used to Be: The Horseman splits him in two at waist.
  • Jerk with a Heart of Gold: He's not the nicest person around, what with his jealousy-driven hostility towards Ichabod. But he does later try to fend off the Horseman in defense of the town, even if that is an ultimately futile task.
  • Too Dumb to Live: Going after an invincible undead mercenary and expecting to come out on top isn't such a great idea. Brave, but incredibly stupid. Especially when said mercenary is clearly a better fighter and barely flinches at gunshots.
  • Troll: Dresses up as the Headless Horseman and chases Ichabod with a flaming pumpkin, which he throws at him. He and a couple men have a laugh about it afterwards.

    Baltus Van Tassel 
Played by: Michael Gambon

  • Asshole Victim: Downplayed. Yes, he, along with the Van Garretts seized the future Lady Van Tassel's land, but he's hardly shown to do much of anything wrong otherwise apart from being somewhat rude to Ichabod after he wrongly accused him of controlling the Horseman.
  • Impaled with Extreme Prejudice: The Horseman impales him with a makeshift harpoon, which he then uses to drag Baltus out of the church he was inside as the Horseman cannot enter hallowed ground.
  • Unwitting Instigator of Doom: By seizing the Archer family land and leaving the future Lady Van Tassel and her sister homeless, he kicked off the entire plot.
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    Dr. Thomas Lancaster 
Played by: Ian McDiarmid

  • The Medic: He appears to be the only doctor in town, apparently handling all medical issues, from surgeries to illness.
  • Redemption Equals Death: Steenwyck bashes his head in with a cross when he tries to confess the conspiracy to Baltus.

    The Burgomaster 
Played by: Christopher Lee

  • The Cameo: For Christopher Lee.
  • Hanging Judge: He makes it clear that he thinks that Ichabod's methods are foolish and that he is willing to throw Ichabod in the cells to rethink his views, not to mention how it is implied that he deals out insanely harsh punishments.
  • Large Ham: Would you expect any less from Christopher Lee? He's only onscreen for a short period of time, but even when he's not yelling, his vocal inflections and booming voice are exactly what you'd expect.
  • Mr. Exposition: Sets the scene for what Ichabod should be prepared for at Sleepy Hollow. Unaware of course, that there is something supernatural at work...

    Young Masbath 
Played by: Marc Pickering

  • You Killed My Father: He joins up with Ichabod to stop the Horseman because the Horseman murdered his father.

    Magistrate Samuel Philipse 

  • The Alcoholic: In every scene he appears, he is seen drinking from a flask of booze. The only time when he doesn't is when he is drinking coffee he mixed with the booze.
  • Bunny-Ears Lawyer: Despite being constantly drunk, he is rather competent at his job and cooperates with Ichabod's investigation.
  • Off with His Head!: The Horseman slices his head off and then collects it.
  • Screw This, I'm Outta Here!: Attempts to do this after assisting Ichabod's inquiries.

    Reverend Steenwyck 
Played by: Jeffrey Jones

  • The Big Guy: He towers over the rest of the elders.
  • Hypocrite: Despite being a minister, he is engaged in a lustful affair with Lady Van Tassel.
  • Only One Name: Unlike the other town elders, we are not told his forename.
  • Sinister Minister: He murders Dr. Lancaster in his own church to stop him from confessing the conspiracy to Baltus.
  • Token Evil Teammate: The other elders seem merely corrupt; he is actively hostile towards Ichabod.
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    Peter Van Garrett 
Played by: Martin Landau

    Notary James Hardenbook 
Played by: Michael Gough

  • Better to Die than Be Killed: His suicide by hanging is implied to be because he believes the Horseman will go after him next and out of guilt for his role in the conspiracy.
  • Cloudcuckoolander: Something clearly isn't right with him.
  • Dropped a Bridge on Him: Hangs himself off-screen, which we only learn about when Lady Van Tassel informs Ichabod.

    Mr. Killian 
Played by: Stephen Waddington

  • Papa Wolf: He holds off the Horseman in a sword duel so his wife and son can escape.
  • Nice Guy: A loving husband and father who is nothing but helpful and polite to Ichabod.
  • Off with His Head!: The Horseman decapitates him, though he doesn't go without a fight.

    Elizabeth "Beth" Killian 
Played by: Claire Skinner

    Lady Crane 
Played by: Lisa Marie

  • Cruel and Unusual Death: After abusing her for her magic, her husband finally decided to kill her by locking the poor woman within an iron maiden.
  • Dark Is Not Evil: She's a brunette dressed in a dark blue gown, but her son describes her as "an innocent child of nature" and has nothing but good to say about her.
  • Domestic Abuse: Her husband really didn't like the fact she had powers.
  • Flight: Possibly. In a flashbask, she levitates above the ground while dancing.
  • Good Parents: By all accounts, a loving mother and a sweet woman.
  • Hot Witch: Courtesy of her Impossibly-Low Neckline and sensual dance in a meadow.
  • Raven Hair, Ivory Skin: Something her son inherited.

    Lord Crane 
Played by: Peter Guinness

  • Abusive Parents: Murdered his wife in front of his son for practicing witchcraft.
  • The Fundamentalist: Strictly religious, to the point of killing his own wife for practicing witchcraft.
  • Light Is Not Good: His church is so white it hurts the eyes. It's also his Torture Cellar, and the place where he murdered his own wife.
  • Opposites Attract: Deconstructed to hell. He was a religious fanatic, and his wife was a witch. It ended nightmarishly bad.

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