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Ichabod Crane
Played by: Johnny Depp, Sam Fior (as a child)
Dubbed by: Bruno Choël (European French)
The protagonist of the film, 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.
- Adaptational Job Change: In the original version, the protagonist Ichabod Crane is the schoolmaster of Sleepy Hollow, whereas in this adaptation he's instead a police constable from New York.
- 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. On the other hand, his deductive techniques do allow him to discover that there is a mundane motivation connecting all the killings, just with the cravat that they're being committed via a supernatural monster.
- 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. And then one last time after the whole affair of freeing the Horseman and defeating Lady Van Tassel.
- Fascinating Eyebrow: His most common reaction to most anything interesting.
- Heroic BSoD: Happens twice. The first time is when he finally comes to realize that the Horseman is indeed real which almost causes him to flee out of Sleepy Hollow, only stopped because he overhears the elders mocking him behind his back and his pride not wanting to give them the satisfaction of outing him as a coward who runs with his tail between his legs. The second time is on a much more somber note when he comes to believe Katrina's the one pulling the Horseman's strings, causing him to leave town out of heartache and disappointment. Thankfully, Ichabod soon realizes his mistaken hypothesis and returns to finally set things right before everything goes to hell.
- Hollywood Atheist: He lost his faith in childhood when he found out that his father tortured and murdered his mother for being a witch.
- Horror Struck: After getting to see the Horseman killing up close for the first time, he spends the next few hours stuck in bed, delirious as all hell by what he saw. Thankfully, he snaps out of it after listening to the elders dismissing him as a coward and realizing that his pride's on the line.
- Human Shield: Ichabod has a tendency to subtly position other people to stand in front of 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. 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 a Flesh Wound: Gets stabbed in the shoulder by the Horseman but has no problem using it.
- 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.
- Token Good Cop: To an extent. He is is the only policeman in New York who uses scientific methods to investigate crimes fairly and logically rather than using brute force and superstition, which gets him packed off to Sleepy Hollow.
- 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!Baltus: Yes, we know. We told you. We all told you.
Katrina Van Tassel
Played by: Christina Ricci
Dubbed by: Barbara Tissier (European French)
The daughter of Baltus Van Tassel.
- 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.
- Adaptational Badass: This version of Katrina is capable of magic, while there was no indication of the original being anything other than an ordinary young woman.
- Big Sister Instinct: When she, Ichabod and Young Masbeth come across the Tree of the Dead, she quickly embraces a spooked Young Masbeth and rubs his back to comfort him after all the heads of the Horseman's victims, which were hidden inside the tree, move forward out of nowhere as if still alive somehow.
- Cute Witch: A pretty doll-faced young woman who regularly practices benevolent magic.
- 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.
- 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.
- Missing Mum: Her mother died prior to the start of the story, since her father has since remarried.
- 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.
- 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 seem to have any issue with the wife her father took after her mother died, though it's clear her mother comes first in her heart. 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.
The Hessian / The Headless Horseman
Click here to see him with his head
Played by: Christopher Walken, Ray Park (headless/stunts)
A fierce Hessian mercenary who was hired by the British to fight against American insurgents during The American Revolution. He was infamous for his love of carnage and for cutting heads off, and ended up killed that way. Then he somehow came back from the dead (without his head) to haunt Sleepy Hollow and cut more heads off.
- Adaptational Badass: While he was said to have fought for the British when he was alive in the original short story, his war record goes unmentioned aside from him being decapitated by a Patriot cannonball and his combat capabilities in life were never brought up. In this movie, though, he's said to have been an excellent fighter who killed enemy soldiers by the dozens.
- 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.
- Dragon-in-Chief: The mysterious Headless Horseman is really the personal assassin of Lady Van Tassel, thanks to her having his head. His invulnerability and might with a sword is the instrument pushing her plans along, while she's just a human. Tellingly, as soon as his head is returned to him, he is easily able to take her back to Hell.
- 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. The Hope Spot of him leaving the Killian's house after killing them before turning back for their son as well seems to be his attempt to defy Lady Van Tassel's commands to kill everybody, only to be compelled to turn back regardless.
- He spares Ichabod, Katrina, and Young Masbath when the former returns his skull to him, and instead drags Lady Van Tassel off to Hell.
- For the Evulz: When he was alive, he didn't care one iota about England's agenda, or about gold. He just loved slaughtering everyone in his path.
- 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.
- Hot Blade: His sword has been heated by the fires of hell to increase its cutting power. As a side effect, it cauterizes any wounds it inflicts resulting in surprisingly clean and bloodless kills. Deconstructed when he stabs Ichabod who survives due to it not being in a vital point and the cauterization preventing him from bleeding out.
- 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 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. Finally, at the end, he allows Ichabod, Katrina, and Young Masbeth to live and returns to Hell with grace, only taking Lady Van Tassel with 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.
- Pay Evil unto Evil: Dragging Lady Van Tassel off to Hell after she used him to carry out a string of murders — including an unborn child — to acquire the Van Tassel estate.
- 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.
- Scary Teeth: He currently provides the trope image for a good reason. He has large, jagged teeth that make him look pretty unnerving.
- Screaming Warrior: Even with his head intact, he's never shown speaking at any point, only his signature war cry, "RAAAAAARRGGHH!!!"
- 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.
- Walking Armory: The Horseman carries three weapons: his sword and a pair of axes as backup weapons. He notably forgoes his sword in favor of the axes when he murders the Killians before bringing out his sword to face Ichabod and Brom. One of the axes is lost when he throws it at the church and it's melted due to either the church being hallowed ground or Katrina's protective enchantment.
- 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)
- Actor Allusion: Once again, Miranda Richardson plays a character who loves a good head-chopping.
- Asshole Victim: Given the number of people she had killed by the Horseman, several who weren't even 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.
- Beneath the Mask: She comes across as a kindly and hospitable lady of the house and genuinely fond of her husband and stepdaughter. However, when she has no reason to keep up that front, she gleefully reveals the true extent of her murderous nature.
- 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, holds Katarina protectively when he renews his intent to locate the Horseman's grave 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.
- Dark and Troubled Past: As a child, she saw her father and mother die in poverty followed by their landlords seizing the family's cottage, leaving her and her sister homeless. Afterwards, Mary/Van Tassel swore revenge on the Van Garretts, the Van Tassels and the entire town of Sleepy Hollow.
- Deal with the Devil: She claims to have made one to ensure her vengeance on the Van Garretts and the Van Tassels.
- Enfant Terrible: She has commanded the Headless Horseman to commit violent murders since she was a young child.
- 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 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.
- Freudian Excuse Is No Excuse: 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.
- Kinslaying Is a Special Kind of Evil: Katrina is disgusted when her stepmother freely admits to killing her own sister just because she helped the heroes, and it's when Mary brushes this off as her simply getting in the way that she loses any shred of sympathy.
- 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.
- Meaningful Rename: She was born Mary Archer but changed her name to Lady Van Tassel after killing a woman with that name and marrying the widower.
- 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.
- Sibling Murder She decapitates her own sister in retaliation for her helping Ichabod.
- The Sociopath: A low-functioning example. Van Tassel has no qualms about murdering her own husband, a young child, or anyone else to achieve her goal of revenge against the Van Garretts and the Van Tassels. She feels no empathy towards anyone, not even her own stepdaughter who she tries to kill or her sister, who was just as much of a victim of the Van Garrets and Van Tassels, whom she personally murders, and maintains a facade of hospitality to mask her murderous, deceitful nature.
- 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.
- White Hair, Black Heart: Has whitish-blond hair and dabbles in black magic.
- Wicked Stepmother: She poisoned the original Lady Van Tassel and married into the family to exact her revenge from within.
- Wicked Witch: She is the witch who manipulated the Headless Horseman into murdering men, women and children.
- 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
- 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 far from the murderous, evil sociopath her sister is.
- 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 aim is 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.
- The Faceless: While we definitely see what she looks like as a child in the flashbacks, the Crone keeps her face hidden during the present day. She wears a thick veil that obscures her features, and the only time she lifts it is to show her Nightmare Face while speaking to Ichabod Crane. However, during the climax there's a recent flashback where her face is shown.
- 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◊.
- No Good Deed Goes Unpunished: Her own sister murders her when she helps Ichabod and uses her powers to assist him with the investigation.
- 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 just as beautiful as her sister.
- Solitary Sorceress: Lives out in the Western Woods by herself and practices spells.
Brom Van Brunt
- Played by: Casper Van Dien
- Adaptational Heroism: While Brom wasn't a complete bastard in the original story, he was still a bully who the narrative heavily implies either manipulated Crane into a confrontation with the Headless Horseman or outright pretended to be him. This version of Brom is no saint either, but he willingly confronts the Horseman in order to protect the other townsfolk.
- 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 at retaliation for attacking him.
- 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 is never a good idea. Brave, but incredibly stupid, especially when said undead merc is clearly a better fighter and immune to gunshots. What's even more stupid is the Horseman clearly giving Brom many chances to back off, only for Brom to keep attacking him until the Horseman finally has had enough of him. The Horseman didn't even bother to collect Brom's head as he should've, leaving Ichabod to deduce that the Horseman is being controlled.
- Troll: Brom dresses up as the Headless Horseman at one point and chases Ichabod with a flaming jack-o-lantern, which he throws at him, causing the inspector to faint. He and a couple of men have a laugh about it afterwards.
Baltus Van Tassel
- Played by: Michael GambonDubbed by: Bernard Dhéran (European French)
- 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.
- Mr. Exposition: He tells the story of the Headless Horseman to Ichabod.
- Pay Evil unto Evil: Personally guns down Reverend Steenwyck when the latter kills Dr. Lancaster.
- 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.
Dr. Thomas Lancaster
- Played by: Ian McDiarmid
- Dirty Old Man: Eventually revealed to have been in a sexual relationship with the Van Tassel's maid, despite being old enough to be her grandfather.
- Heel–Face Door-Slam: His guilt eventually becomes too much to bear and decides to confess his misdeeds, but Steenwyck bashes his head in with a cross when he tries to confess the conspiracy to Baltus.
- Killed Mid-Sentence: "Your four friends played you false. We were devilishly possessed by one who..." BAM! Poor Dr. Lancaster barely even gets to start explaining what he knows about the Archer conspiracy when Rev. Steenwyck grabs a nearby crucifix and uses it to clubber Lancaster, cracking his skull and killing him instantly.
- The Medic: He appears to be the only doctor in town, apparently handling all medical issues, from surgeries to illnesses.
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: He sets the scene for what Ichabod should be prepared for at Sleepy Hollow. Unaware of course, that there is something supernatural at work...
- Small Role, Big Impact: He only has one scene and never reappears, but it involves him sending Ichabod to investigate the crimes in Seepy Hollow, kicking off the plot.
Young Masbath
- Played by: Marc Pickering
- Earn Your Happy Ending: After losing his father and last remaining family, he decides to help Ichabod so he can get justice for him. Not only does he help defeat the villain, he's taken under Ichabod's wing as his protegee in the end.
- Tagalong Kid: The only one brave enough to accompany Ichabod during his investigation, he volunteers his assistance and provides some useful clues that help Ichabod solve the case.
- Take Up My Sword: Uses his father's musket after he's murdered by the Horseman.
- Would Hit a Girl: He knocks out Lady Van Tassel with a heavy stick when she and Ichabod are struggling for the Horseman's skull.
- You Killed My Father: He joins up with Ichabod to stop the Horseman because the Horseman murdered his father.
Magistrate Samuel Philipse
- Played by: Richard Griffiths
- 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.
- No Good Deed Goes Unpunished: He's the one to alert Ichabod that Widow Winship was pregnant when the Horseman killed her with the clue "Five bodies in four graves." However, this leads to the Horseman coming to collect his head when he finally decides to skip town.
- Off with His Head!: The Horseman slices his head off and then collects it.
- Screw This, I'm Outta Here: He attempts to flee after assisting Ichabod's inquiries, but the Horseman literally stops him dead in his tracks.
Reverend Steenwyck
- Played by: Jeffrey Jones
- Evil Is Bigger: He towers over the rest of the elders and turns out to be the only one among them who's truly evil and supportive of the nefarious mastermind behind the Horseman's rampages.
- Hypocrite: Despite being a minister, he is engaged in a lustful affair with Lady Van Tassel.
- Laser-Guided Karma: Steenwyck murders Dr. Lancaster in cold blood to prevent him from confessing the Archer conspiracy to Baltus, only for Baltus to retaliate almost immediately by shooting Steenwyck dead. Judging from Baltus' horrified reaction, he didn't mean to land a fatal shot, but Steenwyck had it coming nevertheless.
- Only One Name: Unlike the other town elders, the audience never gets to hear his forename spoken at any point.
- Sinister Minister: For a man of God, Steenwyck sure has no qualms committing some of the worst mortal sins out of self-servitude. He gladly lends aid to a madwoman's plan to kill several people for monetary gain while having an affair with her, and murders one of his co-conspirators (in his own church, no less!) when the man grows a conscience and tries to admit his crimes.
- Token Evil Teammate: While the other elders seem merely corrupt and are at least shown to be remorseful for having partaken in the conspiracy to destroy the Van Garretts and Van Tassels, Steenwyck is the sole exception. He's actively hostile towards Ichabod and remains unrepentantly supportive of the conspiracy's mastermind until his dying breath.
Peter Van Garrett
- Played by: Martin Landau
- Dead Star Walking: Played by Martin Landau, a famed character actor, and he literally dies before the film reaches two minutes.
- Small Role, Big Impact: Suffice to say, none of the events of the film would have happened if not for him evicting Lady Van Tassel's family many years ago.
- We Hardly Knew Ye: Dies a minute into the film.
Notary James Hardenbook
- Played by: Michael Gough
- Better to Die than Be Killed: His suicide by hanging is implied to be at least partially because he believes the Horseman will go after him next and out of guilt for his role in the conspiracy.
- Cloudcuckoolander: Given his odd mannerisms and rather shifty, secretive behavior, something clearly isn't right with him.
- Dropped a Bridge on Him: He hangs himself off-screen, which Ichabod only learns about when Lady Van Tassel informs him.
- Eye Scream: His left eye appears to be milky-white and blind.
- My God, What Have I Done?: Hardenbook becomes wracked with guilt upon being confronted and interrogated by Ichabod for his role in the conspiracy against the Van Garretts, who lists all of the horrific crimes Hardenbook willingly complied to with Brutal Honesty. This, along with his already growing fear of the Horseman, ultimately drives the old man to commit suicide, something which Ichabod himself didn't expect.
Mr. Killian
- Played by: Stephen Waddington
- Happily Married: He's affectionate with his wife and they are clearly very much in love. His first instinct when the Horseman appears is to call out to her to run.
- 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.
- Papa Wolf: He holds off the Horseman in a sword duel so his wife and son can escape. His last words are yelling at his wife to run for it. Unfortunately, his wife and son end up being killed afterwards.
Elizabeth "Beth" Killian
- Played by: Claire Skinner
- Face Death with Dignity: She faces her decapitation at the hands of the Horseman with quiet resignation.
- Happily Married: She and her husband playfully banter and tease each other and are clearly very much in love.
- Nice Girl: A loving wife and mother.
- Senseless Sacrifice: She uses the few seconds her husband buys her to hide her son under the floorboards and then keeps quiet in the face of death so he won't give himself away... only for the Horseman to find and kill Thomas anyway.
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 practiced witchcraft.
- 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.
