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YMMV / Sleepy Hollow (1999)

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  • Angst? What Angst?: Katrina lampshades this after Brom dies, saying she has "shed my tears for him, and yet my heart is not broken". This is averted when her father dies and she goes into a deep depression.
  • Big-Lipped Alligator Moment: The shot where the Ominous Fog forms hands and douses two torches. Pretty cool-looking, but the Horseman never shows the ability to do anything else like this and isn't normally concerned with keeping his actions subtle.
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  • Complete Monster: Lady Mary Van Tassel, born Mary Archer, is the controller of the Headless Horseman, and the one responsible for his murders. She sought to use the Horseman ever since she was a little girl, betraying him to his death to later enslave his soul to use as her personal assassin. She helped dispose of the first Lady Van Tassel to marry the widower, Baltus Van Tassel. She then sets about consolidating her fortune by eliminating anyone in her path, including the pregnant Widow Winship. When she thinks the Widow Winship might have informed Beth Killian of the pregnancy, Van Tassel sends the Horseman to murder her and her husband, as well as their little boy. She murders her own sister when said sister assists Ichabod Crane in retrieving info on the Horseman and shows no remorse for any of it, simply gloating how she'll have the Horseman murder Ichabod, her stepdaughter Katrina, and their friend Young Masbath, securing her power and fortune.
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  • Creepy Awesome: The Headless Horseman himself, of course.
  • Ensemble Dark Horse:
    • The Killian family, mainly for the father's Dying Moment of Awesome and for being among the nicest of the villagers to Ichabod.
    • Magistrate Philipse has his fans for being the most reasonable of the village elders despite his quirkiness and early death.
    • The Witch of the Western Woods has maybe five minutes of screen time but is a well-liked and well-remembered character for her ties to the villains and Creepy Good status.
    • Brom may not talk much, but his fight with the Horseman and connection to the original story make him fairly popular. And he's also played by Johnny Rico.
    • Young Masbath is seen as a decent and memorable version of the archetypal sidekick character.
  • Evil Is Sexy: Lady Van Tassel. Her Face–Heel Turn is marked with an Evil Costume Switch where her hair goes down and cleavage goes up.
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  • Ham and Cheese: Miranda Richardson is clearly having a ball once the Face–Heel Turn is complete.
  • Harsher in Hindsight: After learning what was in the backroom of his father's church in Ichabod's childhood, his objection to the use of torture devices at the start of the film takes on a more serious light.
  • Hilarious in Hindsight:
  • Moral Event Horizon:
    • Ichabod's father killed his wife in an iron maiden because he thought she was a witch. (The fact that she was is completely beside the point.)
    • Lady Van Tassel crossed the line when she promised her soul to the Devil in exchange for the power to raise the Horseman from the grave as her assassin and use him to murder anyone that stood in her way to acquiring the lands of Sleepy Hollow. The scene that best demonstrates it is when she sent the Horseman to kill the Killian family, including their young son.
  • Narm:
    • At one point, Katrina points out a cardinal and talks about how much she loves them. The cardinal in question is the fakest-looking animatronic bird you've ever seen. Since the film was shot in England, a real cardinal proved absolutely impossible to get a hold of.
    • The scene where the Horseman regains his head is filled with him making strange noises and pretty funny CGI, including his eyes bulging and tongue sticking out. Of course, considering this film, it may be intentional.
  • Narm Charm: Christopher Walken as the not-yet-Headless Horseman should be terrifying, but his Messy Hair and scream can come of as goofy. Nobody is complaining, though.
  • One-Scene Wonder:
    • Christopher Walken plays a pre-headless horseman, and has no lines other than "Shhh" and "Raaa!!", yet there are many people who consider it to be his greatest performance ever. Roger Ebert, in his review, refused to give away Walken's casting, but declared it to be "the only logical choice."
    • Also Christopher Lee, who shows up in one scene at the beginning as the Burgomaster who orders Ichabod to investigate the killings at Sleepy Hollow.
    • Lisa Marie has only three scenes with no dialogue, and yet you definitely remember her as Ichabod's otherworldly mother (and her unbelievably tragic demise).
  • Rewatch Bonus:
    • At the beginning of Ichabod's investigation, Reverend Steenwyck hands him a Bible, claiming that this is the only information he'll need. At first glance, it seems like a case of a small-town preacher being superstitious, but in fact, when Ichabod opens the Bible, he sees a family tree of the villagers' families drawn on the inside cover. The family tree is the invaluable information Ichabod needs to solve the case and one of the conspirators slyly gave him this clue.
    • When Ichabod announces to the household that he intends to find the real culprit for the murders, there's a shot where Lady Van Tassel moves into frame to touch Katrina's shoulders protectively. The true villain marking her Red Herring.
  • Special Effects Failure: The film is de-saturated except for the bright red blood. Despite its unrealistic appearance, this works surprisingly well for both comedy and horror, with the exception of a single scene in the climax, where blood splashes out of the roots of the Tree of the Dead after the restored Hessian and Lady Van Tassel pass through it. For some reason, the blood appears weirdly disconnected from its environment and the shot resembles a rather amateurish B&W colorization.
  • Squick:
    • Reverend Steenwyck and Lady Van Tassel's sex scene, complete with her slicing open her hand and wiping the blood on him. The whole thing taking place in the woods and the eerie music doesn't help either.
    • The Horseman (with his mouth of POINTED TEETH) does a lip-lock with Lady Van Tassel. This cuts the skin around her mouth open, causing blood to spill out.
  • Stoic Woobie: Young Masbath has already lost his mother, and loses his father in the first fifteen minutes of the film. Yet although we see him mourn, he remains quite stoic and dignified, only lashing out when Ichabod suspects Katrina.
  • WTH, Casting Agency?: Does Christopher Walken sound like the first name to come to mind when casting the Headless Horseman? Not for many. But it's awesome.
  • The Woobie: Katrina has already lost her mother at the start of the film. She soon loses her suitor, stepmother, and father, the latter of whom is killed in front of her. Then she finds out her mother was murdered by her stepmother, who then tries to kill her!

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