WARNING: Only spoilers from the current season (Season 3) are whited out.
The Four Horsemen of the Apocalypse
Abraham Van Brunt AKA The Headless Horseman/Death
An undead man who sold his soul to Moloch after being killed by The Shadow Warriors. His head was later severed by his former best friend, a former history professor-turned Revolutionary War captain Ichabod Crane, causing him to become known as the Headless Horseman.
Both Abraham and Crane were later resurrected in 21st-century Sleepy Hollow, where he was revealed to be the First of the Four Horsemen of the Apocalypse: Death.
- Adaptational Villainy: In The Legend of Sleepy Hollow, Abraham (better known by his nickname "Brom Bones") was the local hero who played a prank on Ichabod by pretending to be the Headless Horseman. This version of Abraham is the Headless Horseman.
- Arch-Enemy: To Ichabod.
- An Axe to Grind: The Horseman's super-heated broad axe.
- Badass Longcoat: A Redcoat of the British army, to be specific.
- Bald of Evil: Back when he had a head.
- Big Bad Friend: Abraham was once Ichabod's best friend before dying and selling his soul.
- The Brute: His main function. He's the chief physical threat of the series, but he's really not that smart. Katrina has spent most of season 2 playing mind games with him.
- Bond Villain Stupidity: In Magnum Opus, he has both Ichabod and Lieutenant Abby Mills at his mercy, he has the perfect opportunity to kill them both and what does he do? He buys their BS lies that there is no Sword of Methusealah a powerful weapon that can kill anything, even demons, and leaves when Moloch's trumpet sounds. His love for Katrina has also proved instrumental in her undermining schemes.
- The Bus Came Back: After being Put on a Bus at the start of season 3 he returns for the finale to help Ichabod kill the Big Bad.
- Combat Pragmatist: Expect him to open fire on an unarmed foe very often.
- Composite Character: He and the Horseman are made into one character.
- Co-Dragons: With the other Horsemen of the Apocalypse.
- Deal with the Devil: He made a deal with Moloch in order to get what he wanted most—Katrina.
- Disposable Fiancé: Katrina broke off their engagement because she wanted to Marry for Love.
- Dragon-in-Chief: He's technically a subordinate to Moloch, but he is the main threat until the Season 1 finale.
- Dragon Ascendant: With Moloch gone after his death in "The Akeda", some of his demonic servants have pledged their loyalty to Abraham.
- Entitled to Have You: His attitude towards Katrina.
- Evil Former Friend: Abraham was a friend of Ichabod, and now he's his worst enemy.
- Fallen Hero: He and Ichabod were once on the same side. Though that side wasn't the same conflict as the hellish one at all.
- Fan Disservice: The viewers of the first episode of season 2 are treated to a view of Abraham shirtless... still missing his head.
- Flaming Sword: Or Flaming Axe as the case may be. It goes to 500 degrees, as mentioned above.
- Forgotten Friend, New Foe/We Used to Be Friends: With Ichabod.
- From Nobody to Nightmare: He's actually Ichabod's old best friend Abraham. He was left heartbroken by Katrina rejecting him after their relationship seemed so strong and lost his temper during a mission when Ichabod admitted that Katrina had rejected Abraham for him. Him losing it resulted in him being shot and captured by Moloch's Hessians, at which point he made a Deal with the Devil and became the Horseman of Death out of anger, jealousy, heartache and a desire for vengeance.
- Genius Bruiser: Had to be one to learn how to wield modern weaponry expertly in less than a week after previously only being familiar with 18th century weaponry.
- Headless Horseman: He's headless and he rides a horse.
- The Heavy: The Horseman isn't technically the main villain, but he drives much of the plot and is the Arch-Enemy for Ichabod and Abbie. Jeremy usurps this position in Season 2 for the most part.
- Hell-Bent for Leather: Wears leather in the present day.
- Hellish Horse: His "pale horse" has bright red eyes.
- Hopeless Suitor: With a touch of Unrequited Tragic Maiden, but he seemed more interested in possessing Katrina than having her return his feelings.
- Honor Before Reason: Even as a merciless undead killer, he still has a high amount of honor. During the episode Magnum Opus, He has Ichabod at his mercy, and is about to kill him, and somehow Ichabod manages to get him to grant him the honor of a duel. Ichabod never expected to win, and was just stalling for time.
- Horsemen of the Apocalypse: The Horseman is interpreted as one of them (Death, specifically).
- Implacable Man: Ichabod at one point says "Nothing will stop the Horseman," which isn't a hyperbole at all.
- Losing Your Head: Couldn't be a Headless Horseman without this.
- Love Makes You Evil: Katrina's rejection lead him to make a deal with Moloch and become the Horseman.
- Malevolent Masked Man: In life, with a blackened skull mask.
- Menacing Stroll: He never runs.
- More Dakka: He's got an assault rifle and a shotgun, neither of which ever seem to run out of ammunition or require reloading.
- Murder the Hypotenuse: Why he wants to kill Ichabod.
- No Name Given: Subverted. Unlike in the original story, we do get an origin for the Horseman.
- Noble Demon: His love for Katrina is what drives him to try and repeatedly and kill his former best friend, and to sell his soul to Moloch, but it also tethers his last remaining shred of humanity.
- Off with His Head!: Crane himself relieves the Horseman of his head in this interpretation. The Horseman inflicts it on many other victims throughout.
- Pet the Dog: Repeatedly attempts to save Katrina from Henry, up to and including nearly getting incinerated.
- Prophet Eyes: The Horseman had these when he had a head. The head itself still has them.
- Put on a Bus: He's unceremoniously taken out of the picture at the start of season 3 by the newest Big Bad. He returns in the finale for some payback.
- Sealed Evil in a Can: The Horseman has been locked in a chained-up coffin at the bottom of a river for the last 250 years, but now has been unleashed again by Moloch.
- Shotguns Are Just Better: His most recurring weapon (besides the axe) is a shotgun.
- The Voiceless: Of course, not having a head might have something to do with it, but one should note he was also this in life. As the Horseman, anyway; however, when he speaks through Andy Brooks, it's in a deep, not quite human voice. In the second season he uses the amulet he gave Katrina to appear to her in his original form in which he can speak.
- Walking Armory: He carries a rather preposterous amount of weapons on his back.
- Walking Spoiler: Due to his true identity.
- Was Once a Man: The Headless Horseman was originally Ichabod's friend, Abraham.
- Weakened by the Light: The Horseman is burned by sunlight. Hence why he only appears at night.
- Wild Card: With Moloch gone he has no master to serve, and therefore the only things that motivate him now are his lust/love for Katrina and his hatred for Ichabod. In "Paradise Lost Katrina offered to remove his soul from Death, so that he will be a man again. He seemed to accept her offer, but then turned around and was ready to lead Moloch's former servants.
- Yandere: For Katrina, enough to sell his soul to Moloch to get her and kill Ichabod.
The Third of the Four Horsemen of the Apocalypse. He appears as a Japanese Samurai wielding a bow riding a black horse.
- Dark Is Evil: His armor and his horse.
- The Dreaded: Due to being a Horseman of the Apocalypse.
- The Last of These Is Not Like the Others: The only Horsemen so far who wasn't previously a mortal with ties to Crane.
- Malevolent Masked Man: Resembles a samurai carrying a bow.
- Mystical Plague: Spreads what may or may not have been the Black Plague across Roanoke Island. Said plague would allow him to manifest in the real world should it successfully spread.
- Red Eyes, Take Warning: His horse.
- The Spook: In some ways, more than Death.
The Horseman of War (Jeremy Crane/Henry Parish)
One of the four horsemen.
Major Supernatural Antagonists
"The God Demon of Child Sacrifice," with the goal to bring forward the Apocalypse. As such, he was responsible for the raising of the Headless Horseman.
Moloch's appearance is sometimes blurred out, but he appears as a humanoid, with claws, horns, and demonic voice, speaking Greek. It has demonstrated invisibility, knowledge in magic spells, telekinesis, teleportation, and massive strength. He resides in the parallel dimension known as "Purgatory."
- Big Bad: The entire plot revolves around his attempts to begin the Apocalypse, even though his Horsemen of the Apocalypse are the most often seen threats. That is, until "The Akeda". Then Abraham appears to pick up the slack.
- Bad Boss: Failure is a one-way street with him. He also shows no respect to his Horsemen, especially in "The Akeda", where Henry/Jeremy points out to him that Katrina is Abraham's despite the fact that he was told to sacrifice her to bring about The End of the World as We Know It for real, and beforehand, he is told that he is not the first, nor will he be the last, driver of the Horseman of War. This combination of effects leads him to try to kill the demon once and for all.
- The Blank: He's been described as faceless, but since he's only ever been seen blurred-out, the audience can't be sure. That is, until "The Akeda", where he's seen fully with his risen form.
- Evil Sounds Deep: Well, he is a demon after all.
- Hidden Agenda Villain: Nobody has figured out yet why he's trying to trigger the Apocalypse.
- Horned Humanoid: Possess giant, demonic horns.
- Large and in Charge: Towers over every other character he's been seen near.
- Meaningful Name: He gains a name in the fourth episode. Moloch means "king" and the Canaanite god is known for child sacrifice.
- Mirror World: Lives in one, Purgatory to be specific.
- Our Demons Are Different: Lives in a Mirror World in Purgatory, but can interact with the mortal realm as well.
- Pragmatic Villainy: One reason he may have revived Brooks. Spies and gofers are useful after all, even if they're zombies.
- Undercrank: Used to terrifying effect for his movements in Season 1.
- Arch-Enemy: To Jenny, who he once possessed and in the process completely traumatized her.
- Body Surf: Its whole schtick. Ancitif jumps from body to body via touch.
- Evil Sounds Deep: No matter what body it's possessing, Ancitif has a deep baritone.
- I Shall Taunt You: It likes to do this.
- Mouth of Sauron: Ancitif acts as a messenger of Moloch, passing on his various prophecies and threats.
Minor Supernatural Antagonists and Monsters Of The Week
An evil dream spirit, attacking people in their dreams.
- The Blank: Partially, since the place his mouth would be is covered by a flap of skin.
- Driven to Suicide: What he ultimately does to people.
- Eye Scream: What he does to his victims, and once they've died, their eyes will essentially deflate and show the sand that was inside them.
- Eyeless Face: He has two dark and empty eye sockets, which he also inflicts on his victims.
- Sadly Mythtaken: No such creature exists in any version of Mohawk mythology.
A vicious beast resembling a humanoid stitched doll. He was the protector of Ichabod's son Jeremy.
- Blood Magic: The method by which he is created, and how he is killed.
- Impaled with Extreme Prejudice: By Ichabod, using a shard of glass stained with blood.
- Papa Wolf: With Ichabod gone, the Golem served as the closest thing Jeremy had to a father, acting as his tireless protector.
- Sadly Mythtaken: Its resemblance to the traditional Golem of Jewish lore is...tenuous, at best.
- Godzilla Threshold: Abbie and Crane both acknowledge that something strong enough to take on the Headless Horseman is a dangerous gambit. Especially when the final component is the Horseman's head.
- In-Universe Nickname: Franklinstein's Monster. because it was Franklin who created it.
- Noble Demon: He's a supernatural creature who wears the head of the Headless Horseman but so far he seems to fit this, shown well in that Abbie's hesitation about waking him up seems to vanish after he directly saves her from the Horseman of War.
The Pied Piper
Not the Pied Piper, but a Pied Piper. A mercenary who sold his soul to Moloch, but wound up betrayed by his employer. Now he exists as a curse on the mans descendants.
- Adaptational Badass: From rat catcher and child abductor, to a supernaturally powered assassin.
- Dark Is Evil: A remorseless killer, dressed all in black.
- Musical Assassin: Uses his flute to lure and entrance his victims, after which he kills them.
- Super Speed: One of the gifts he got from Moloch.
- Would Hurt a Child: Abducts and kills the eldest daughter of his employers family when they turn ten.
The Weeping Lady/Mary Wells
A local legend of Sleepy Hollow. A supposedly benign spirit that begins attacking women close to Crane. Her real identity is that of Mary Wells, Ichabod's former fiancée, who died while trying to win him back; responsible for her return from the dead is Henry, who once more wants to cause trouble for his father.
- Clingy Jealous Girl: While still alive, she accused Katrina of bewitching Ichabod. When undead, she simply tries to kill any woman in his vicinity.
- Ethereal White Dress: Subverted. She is based on the ghostly La Llorona of Latin American myths. In contrast to her inspiration, however, she's shown wearing all black.
- Stringy-Haired Ghost Girl: Thanks to her watery grave.
- Yandere: She does not take kindly to women flirting with Ichabod. Or talking to Ichabod. Or standing right next to Ichabod. Poor Caroline pays the price for her anger, and Abbie narrowly escapes the same fate.
A deadly creature of Algonquin legend, the wendigo is half man and half animal, a predator that has an intense hunger for blood and human organs. Fighting him is made very difficult for Abbie due to him being the son of her old mentor, Sheriff Corbin.
- Blood Lust: The Wendigo has a strong appetite for human blood. The hunger and transformation process is triggered when in the vicinity of blood, and can only turn into human form after it consumes human organs.
- Horned Humanoid: Much like in the original myths, the Wendigo sports a pair of antlers.
- I'm a Humanitarian: Like most Wendigos, it feeds on human flesh and organs.
- Skinwalker: Described as such by Ichabod.
- Wendigo: Naturally, though he didn't come by it on his own accord - Henry cursed him to transform and later tries to make it permanent.
A demonic monster that feeds on a person's life force, choosing its victims by seeking out people who bear a strong desire for another. Secret desires are especially attractive to them. This flavour of succubus is known as the Incordata, or "The Heartless", as in that it has no heart which is stored separately from its body.
- Achilles' Heel: The Incordata's one major weakness is the fact that its heart is stored outside of its body, making it vulnerable to attack. To kill the creature, you must first destroy the heart and then its body.
- Brief Accent Imitation: Adopts an English accent similar to Katrina's when it tries to seduce Ichabod.
- Horny Devils: Played with. You'd think being a succubus, that she requires sex to drain someone's life force. This type of succubus only requires being near someone to drain out their energy.
- Life Drinker/Vampiric Draining: Succubi feed by draining people's life force and attacking a person's vital points.
- Kill It with Fire: Abbie and Katrina kill it by burning its heart.
- No Name Given: Its name isn't said in show, but is credited as Lilith.
- Red Eyes, Take Warning: When its eyes glow red: run.
- Shapeshifting Seducer: Of a variety. The succubus changes her appearance on a cosmetic level to suit someone's "type"; such as putting on a pair of glasses for the victim that was into a girl with spectacles, or putting on a corset to match Katrina's appearance when it attempts to manipulate Ichabod, or dressing like Abbie when it draws in Nick Hawley.
- The Vamp: Literally and metaphorically.
The GorgonAn ancient creature that guards the Sword of Methuselah.
- Taken for Granite: Like most gorgons, one look and boom, you're stone.
Other Supernatural Characters
Nurse Gina Lambert
Gina Lambert was a nurse employed by Tarrytown Psychiatric in the 1950s, where it was discovered she was murdering her own patients. She was executed for her crimes, but now haunts the hospital where she used to work and forcing people to commit suicide.
- Bitch in Sheep's Clothing: Seems sweet and helpful to her patients, but is really manipulative and malicious and will merrily convince you to kill yourself while watching and smiling.
- Black Eyes of Evil: In her final battle, she drops all the pretense and goes full out dark side.
- Ghostly Goals: "Helps" her patients find peace by giving them a nice dose of psychotropic drugs to lower their defences so she can use her powers of maipulation to have them commit suicide.
- Jacob Marley Apparel: Still dressed in her nurse's uniform.
- Mercy Kill: Believed that her patients were in pain and chose to end their suffering... By forcing them to take their own lives.
- Poltergeist: Along with access to lethal drugs, she is also unfortunately a psychotic undead bitch with immense telekinetic power and the power of suggestion.
- Serial Killer: Of the "Angel of Mercy" type.
A zealot angel who escaped Purgatory. As a former member of the Heavenly Host, Orion wishes to purge the world of all sin.
- Affably Evil: Honestly he's reasonably friendly for a deranged, murderous angel.
- Angelic Beauty: For a murderous angel responsible for civilisation-wide death, he's pretty easy on the eyes.
- Ax-Crazy: Talks about murdering the Horseman and cleansing Sleepy Hollow (read: levelling and burning it to the ground) with a psychotic glint in his eyes.
- Beethoven Was an Alien Spy: Was the angel that visited George Washington and was probably responsible for the destruction of Pompeii and lot of other disasters.
- Blood Knight: Very eager to fight and shed the blood of evil with zeal. As well as innocent people.
- Dark Is Evil: Has black wings, wears dark clothes and unable to differentiate between good and evil.
- Fallen Angel: It's never specified whether he was sent from High Above, or fell, but he has a lot of the elements associated with the tropes (cold, a skewed sense of morality, gleeful at the prospect of combat due to a lack of restraint).
- Good Wings, Evil Wings: The black wings should have been a sign that he's not totally on the up-and-up.
- Harbinger of Impending Doom: Only appears before a great catastrophe because he's the one that causes them.
- He Who Fights Monsters: Has "cleansed" so much evil and sin that it's nearly impossible for him to see goodness of mankind. Though he still finds sunrises pretty.
- Knight Templar: He's more or less this, he wants to bring better times for mankind, unfortunately his method for doing this is by pretty much exterminating everything he see's as tainted by evil.
- Nigh-Invulnerability: He's able to shrug of bullets with next to no reaction, it takes a being of incredible power such as the Horseman of Death to kill him.
- Rings of Death: Wields a pretty cool looking chakram.
- Soft-Spoken Sadist: Has a soft voice, which makes his murderous and genocidal intent even more obvious.
- The Stoic: Almost never raises his voice, and yet his murderous glee is even more prominent.
A small time painter, temporary member of Washington's social circle, notorious people-hanging blood-draining serial killer. He committed a heinous series of murders in the 1770s until he was trapped in an enchanted painting by Abigail Adams and Reverend Knapp.
- The Alcoholic: A major reason why his art career didn't really take off. As Katrina put it, "he favored port more than paint".
- Blood Is the New Black: Completely drenched in a terrifying amount of blood. He must be a very messy artist.
- Freudian Excuse: Apparently he was discouraged from his artistic pursuits as a child, through rather violent means.
- Mad Artist: Ask yourself this: would a sane person paint with someone else's blood?
- Phantom Zone Picture: Trapped within a painting of the attic in his family house by the Sisterhood of the Radiant Heart on request from Abigail Adams. However, when the painting is activated in the modern day, he is able to temporarily leave the painting to find victims and complete his blood ritual.
- Serial Killer: Murdered people by hanging them upside down and slitting their carotid arteries, draining them of their blood. In the modern day, he commits the same murders, but uses his victims' blood in order to complete a portrait of the Hanged Man (in the Tarot's Major Arcana) and free himself from the painting.
- Spooky Painting: The painting changes whenever he moves or leaves to find another victim, and it is bloody terrifying (pun not intended).
- Starving Artist: Often painted portraits in exchange for room and board, so that should tell you something about his financial situation.