YMMV / Sleepy Hollow (1999)

• Aluminum Christmas Trees: One might think that Katrina having a book of spells and practicing white magic might be a fanciful historical liberty taken by the filmmakers, especially given the Christian prohibition against witches. However, folk charms and healing, often done within a Protestant Christian context, were not unheard of in rural communities.
• 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.
• Audience-Coloring Adaptation: In the 2000s, it was common for fans of Washington Irving's short story to stress that this film was only loosely inspired by it; for one, there is no beheading spree, there are no Wicked Witches in the short story, Ichabod is much less sympathetic, Brom is to be viewed as heroic and it's left vague whether or not the Headless Horseman is a "Scooby-Doo" Hoax.
• 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.
• Catharsis Factor: Lady Van Tassel being Dragged Off to Hell by the Horseman once his head is restored to him.
• 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.
• 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.
• Ham and Cheese: Miranda Richardson is clearly having a ball once her character's revealed to be Evil All Along.
• 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.
  • Reverend Steenwick is revealed to be a Covert Pervert having a fiery affair with Lady Van Tassel. This is almost classy compared to the Real Life scandal that ended Jeffrey Jones's career.
• He Panned It, Now He Sucks!: Back in her days as The Nostalgia Chick, Lindsay Ellis did a very mocking video of the film, indicating she thought poorly of it. For those who hated her Nostalgia Chick days, said video is often used as a comparison for how bad her old content was.
• 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 they share scenes together and the exact opposite happens. Even funnier considering who plays the Horseman's fight double and how Count Dooku dies! Furthermore, the Horseman, played by Ray Park, wins a battle by cutting someone in half. Just months earlier, he played the loser who suffers the same fate. (Bonus points: Sleepy Hollow was largely filmed in the same studio^*Leavesden Film Studios as The Phantom Menace immediately after that film vacated the set.)
  • 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 The Lord of the Rings film series. This leads to amusing situations, such as Dumbledore and Uncle Vernon sharing the screen with Emperor Palpatine, and mighty wizards Dumbledore and Saruman turning up in the same movie (although not onscreen together, sadly). For bonus points, Captain Jack Sparrow fights off Darth Maul during all the fight scenes. Oh and Rita Skeeter is married to Dumbledore.
  • Given Christina Ricci's tendency to play dark and/or weird characters, it's very ironic that the one film she does with Tim Burton, she plays against type as a seemingly benevolent White Mage. She's a Red Herring and turns out to be Good All Along.
  • The film ends with the villain's hand sticking out of a tree stump, looking much like the protagonist's in Corpse Bride.
  • Christina Ricci playing the female lead in a Tim Burton movie with a hidden villain seeking death through supernatural means, is funny how she would later play the hidden villain in another Burton-related property, Wednesday.
• Magnificent Bastard: The Headless Horseman was a Hessian mercenary fighting in the Revolutionary War, and was infamous for filing his teeth to points in order to terrify his enemies as he rode across the battlefield chopping off heads. After being run down and killed in the woods on the outskirts of Sleepy Hollow, Mary Van Tassel uses his skull to command him to rise from the grave to kill their enemies. After killing multiple townsfolk with ruthless efficiency, the Horseman's skull is returned to him by Ichabod Crane, breaking his master's control over him. The restored Horseman spares Ichabod and his friends and instead claims his former master as his final victim, returning to Hell with a triumphant cry.
• 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.
• Nausea Fuel: The scene where Ichabod chops through the wood at the Tree of the Dead, and splashes of blood keep spilling out. Even those who aren't haemophobic would be very Squicked out.
• One-Scene Wonder:
  • Christopher Walken plays a pre-decapitated 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).
• Questionable Casting: Does Christopher Walken sound like the first name to come to mind when casting the Headless Horseman? Not for many. But it's awesome.
• Special Effect 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.
• Spiritual Successor:
  • The movie is something of an updated Hammer Horror production- It shares Hammer's penchant for making drastic adaptation changes, involving much more sensuality and violence, and even has two Hammer alumni in Christopher Lee and Michael Gough.
  • Produced by Francis Ford Coppola, Sleepy Hollow is, in a sense, a follow-up to Coppola's other two Darker and Edgier 90's horror adaptations- Bram Stoker's Dracula (which Coppola directed) and Mary Shelley's Frankenstein (which he produced).
• 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.
• They Wasted a Perfectly Good Character: Young Thomas Killian, who could have provided some interesting exposition and gravitas if he'd survived the deaths of his parents, and whose death feels like gratuitous when he isn't even among the people that Lady Van Tassell mentions knew too much (the Horseman even seems to kill him solely as an afterthought). Tim Burton flat out said that the boy died purely because Burton hates that children are always spared from danger in horror films.
• 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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