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YMMV / Sleepy Hollow (1999)

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  • Big-Lipped Alligator Moment: The shot where the 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.
  • Complete Monster: Lady Mary Van Tassel, born Mary Archer, is the controller of the Headless Horseman, and the one responsible for his murders. Van Tassel 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. Van Tassel then sets about consolidating her fortune by eliminating anyone in her path, including a pregnant widow. When she thinks the widow might have informed another woman 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, securing her power and fortune.
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  • Creepy Awesome: The Headless Horseman himself, of course.
  • Evil Is Sexy: Lady Van Tassel.
  • Harsher in Hindsight: After learning what was in the back room of the 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: In this movie, Christopher Lee's character survives and Ian McDiarmid's character dies. Fast forward six years to the next time share scenes together, and the exact opposite happens. Even funnier considering who plays the Horseman's fight double, and how Count Dooku dies!
    • The casting in general gets pretty hilarious in hindsight if you think about the roles so many of the actors went on to play - in addition to the Star Wars examples above, other actors went on to have prominent roles in the Harry Potter and Lord of the Rings film series. This leads to amusing situations, such as Dumbledore sharing the screen with Emperor Palpatine,and mighty wizards Dumbledore and Saruman turning up in the same movie (although not onscreen together). For bonus points, Captain Jack Sparrow fights off Darth Maul during all the fight scenes.
  • Moral Event Horizon:
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    • Ichabod's father killed his wife in a torture device because he thought she was a witch. (The fact that she was is completely beside the point.)
    • Lady van Tassel, she 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 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.
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  • 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 magistrate who orders Crane to investigate the killings at Sleepy Hollow.
  • Rewatch Bonus: At the beginning of Ichabod's investigation, one of the villagers hands him a Bible, claiming that this is the only information he'll need. At first glance it seems like a case of small town people being superstitious, but in fact when Ichabod opens the Bible, he sees a family tree of the villagers' families drawn in 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.
  • Special Effects Failure: The film is desaturated 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 Dead Tree after the 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 colourisation.
  • Squick: The Horseman (with his mouth of POINTED TEETH) does a liplock with Lady Van Tassel. This cuts the skin around her mouth open, causing blood to spill out.
  • 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.

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