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    Ichabod Crane 

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

Played by: Johnny Depp

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.
  • Hollywood Atheist: Lost his faith 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.
  • Kid Detective: Ichabod is described by Tim Burton as a thirteen-year-old girl detective in a man's body.
  • 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 Cute Witch Katrina Van Tassell.
    • 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 realises 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: Ichabod Crane. The reason he's sent to investigate the events on 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 Crane to accept it...)
  • Screams Like a Little Girl: Actually not played straight at all, surprisingly, given his Cowardly Lion nature. He does have 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 the Magistrate being beheaded right in front of him, he freaks out and says this to the townsfolk. They believe him of course, but up until then they 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.
  • Hair of Gold, Heart of Gold: She's a sweet-natured blonde.
  • 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 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.
  • Missing Mum: Her mother died prior to the start of the story, some time ago since her father has since remarried.
  • Pimped-Out Cape: Katrina greets Ichabod and Young Masbeth 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 Ichabod's 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.
  • 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 

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

  • 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.
  • 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.
  • Even Evil Has Loved Ones: He looked genuinely devastated when his horse, Daredevil, was shot.
  • Even Evil Has Standards: While he thoroughly enjoys senseless butchery, he refuses to murder children when he can help it, and he spares Ichabod, Katrina, and Masbeth 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 victims 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.
  • 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 fearsomeness.
  • Noble Demon: As the Headless Horseman, he's actually nicer than he was when he was alive. He only kills because he's commanded to, and once he gets his skull back, he's livid with the one controlling him. Also notable that even in his previous life, he refused to harm children and mourned the death of his horse.
  • No Good Deed Goes Unpunished: He stays behind when his horse get 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 Garrets 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.
  • 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.
  • 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 soldiers. All he did was shush them. This completely goes out the window upon his resurrection, when he murders the young Thomas Killian, although notably, he only did so because he was under the command of Lady Van Tassel.

     Lady Van Tassel 

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

  • Ax-Crazy: Aside from using a literal axe on two of her victims, she becomes a lot more 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 is appears to mourn the death of Notary Hardenbrook, but she is actually responsible for nearly everything that's gone wrong.
  • Deal with the Devil: She claims to have made one to ensure her vengeance on the Van Garretts and the Van Tassels.
  • Freudian Excuse: The Van Tassels and the Van Garrets 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, 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.
  • Lady of Black Magic: Mary Van Tassel is quite an attractive woman, who acquired her power to control the Horseman through a Deal with the Devil, 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 her own sister, and Sarah.
  • Wicked Stepmother: She poisoned the original Lady Van Tassel and married into the family to exact her revenge from within.
  • Your Cheating Heart: Has an affair with the Reverend Steenwyck behind her husband's back.

     The Crone 

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

  • Creepy Good: "Good" might be a bit of a stretch, since we don't know much about her and she does practice black magic, 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".
  • 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.

     Brom Van Brunt 

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

Played by: Casper van Dien

  • Death by Adaptation: While in the original story he makes it out much better than Ichabod, here he's got one of the most violent and gory of the deaths.
  • Death by Irony: He dressed up as the Horseman to scare Ichabod, only to fall prey to the real Horseman's blades later.
  • Demoted to Extra: In the book, he's Ichabod's rival and the one Katrina chooses over him, as well as the fake Headless Horseman. Here, his role is considerably tuned down.
  • Half the Man He Used to Be: The Horseman splits him down the middle.
  • Jerk with a Heart of Gold : He's not the nicest person around, what with his largely unjustified hostility towards Ichabod. But he does later try to fend off the Horseman, 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.
  • 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

  • Impaled with Extreme Prejudice: The Horseman impales him with a harpoon, which he then uses to drag Baltus out of the church he was inside as the Horseman cannot enter hallowed ground.
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    Dr. Thomas Lancaster 
Played by: Ian McDiarmid

  • The Medic: Lancaster 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 about the conspiracy to Baltus.
  • Your Cheating Heart: He is having an affair with the Sarsh, the Van Tassel's servant.

    Burgomaster 
Played by: Christopher Lee

  • The Cameo: For Christopher Lee.
  • Hanging Judge: The Burgomaster makes it clear that he thinks that Crane’s methods foolish and he makes it clear he is willing to throw Crane in the cells to “rethink” his views, not to mention how it is implied that he deals out insanely harsh punishments.
  • 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 Crane 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 Crane’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 enquiries.

    Reverend Steenwyck 
Played by: Jeffrey Jones

  • Hypocrite: Despite being a minister, he is engaged in a lusty affair with Lady Vsn 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.
  • 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

    Mr. Killian 
Played by: Stephen Waddington

  • Papa Wolf: He holds off the Horseman in a sword duel so his 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.

    Claire Killian 
Played by: Claire Skinner

    Lady Crane 
Played by: Lisa Marie

  • Good Parents: By all accounts a loving mother and a sweet woman.

    Lord Crane 
Played by: Peter Guinness

  • Abusive Parents: Murdered his wife in front of his son Ichabod for practicing witchcraft.
  • The Fundamentalist: Strictly religious, to the point of killing his own wife for practicing witchcraft.

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