Line #10 YMMV/SleepyHollow1999


1	* AluminumChristmasTrees: One might think that Katrina having a book of spells and practicing [[spoiler: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.
2	* AudienceColoringAdaptation: 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 [[OffWithHisHead beheading]] spree, there are no {{Wicked Witch}}es 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 HeadlessHorseman is a ScoobyDooHoax.
3	* BigLippedAlligatorMoment: The shot where the OminousFog 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.
4	* CatharsisFactor: [[spoiler:Lady Van Tassel]] being DraggedOffToHell by the Horseman [[spoiler:once his head is restored to him]].
5	* CompleteMonster: [[spoiler:[[TheManBehindTheMan Lady Mary Van Tassel]], born Mary Archer, is the controller of the HeadlessHorseman, and the one responsible for his murders. She sought to use the Horseman ever since she was a [[EnfantTerrible 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 [[InheritanceMurder 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 [[WouldHurtAChild 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.]]
6	* CreepyAwesome: The Headless Horseman himself, of course.
7	* EnsembleDarkHorse:
8	** The Killian family, mainly for the father's DyingMomentOfAwesome and for being among the nicest of the villagers to Ichabod.
9	** Magistrate Philipse has his fans for being the most reasonable of the village elders despite his quirkiness [[spoiler:and early death]].
10	** 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 CreepyGood status.
11	** 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 [[Film/StarshipTroopers Johnny Rico]].
12	** Young Masbath is seen as a decent and memorable version of the archetypal sidekick character.
13	* HamAndCheese: [[spoiler: Miranda Richardson]] is clearly having a ball once [[spoiler: her]] character's revealed to be EvilAllAlong.
14	* HarsherInHindsight:
15	** After learning [[spoiler: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.
16	** Reverend Steenwick is revealed to be a CovertPervert having a fiery affair with Lady Van Tassel. This is almost classy compared to the RealLife scandal that ended Creator/JeffreyJones's career.
17	* HePannedItNowHeSucks: Back in her days as WebVideo/TheNostalgiaChick, Creator/LindsayEllis 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.
18	* HilariousInHindsight:
19	** In this movie, Creator/ChristopherLee's character survives and Creator/IanMcDiarmid's character dies. Fast forward six years to the [[Film/RevengeOfTheSith next time]] they share scenes together and the exact opposite happens. Even funnier considering [[Creator/RayPark who plays]] the Horseman's fight double and [[OffWithHisHead how Count Dooku dies]]! Furthermore, the Horseman, played by Creator/RayPark, wins a battle by cutting someone in half. Just months earlier, [[Film/ThePhantomMenace he played the loser who suffers the same fate]]. (Bonus points: ''Sleepy Hollow'' was largely filmed in the same studio[[labelnote:*]]Leavesden Film Studios[[/labelnote]] as ''The Phantom Menace'' immediately after that film vacated the set.)
20	** 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 ''Franchise/StarWars'' examples above, other actors went on to have prominent roles in the ''Franchise/HarryPotter'' and ''Film/TheLordOfTheRings'' film series. This leads to amusing situations, such as [[Creator/MichaelGambon Dumbledore]] and [[Creator/RichardGriffiths Uncle Vernon]] sharing the screen with [[Characters/StarWarsEmperorPalpatine Emperor]] [[Creator/IanMcDiarmid Palpatine]], and mighty wizards Dumbledore and [[Creator/ChristopherLee Saruman]] turning up in the same movie (although not onscreen together, sadly). For bonus points, [[Creator/JohnnyDepp Captain]] [[Franchise/PiratesOfTheCaribbean Jack Sparrow]] fights off [[Creator/RayPark Darth Maul]] during all the fight scenes. Oh and [[Creator/MirandaRichardson Rita Skeeter]] is married to Dumbledore.
21	** Given Creator/ChristinaRicci's tendency to play dark and/or weird characters, it's very ironic that the one film she does with Creator/TimBurton, she [[PlayingAgainstType plays against type]] as a seemingly benevolent WhiteMage. [[spoiler: She's a RedHerring and turns out to be GoodAllAlong]].
22	** The film ends with the villain's hand sticking out of a tree stump, looking much like the protagonist's in WesternAnimation/CorpseBride.
23	** Creator/ChristinaRicci playing the female lead in a Creator/TimBurton movie with a hidden villain seeking death through supernatural means, is funny how she would later [[spoiler:play the hidden villain]] in another Burton-related property, ''Series/{{Wednesday}}''.
24	* MagnificentBastard: The Headless Horseman was a Hessian mercenary fighting in the Revolutionary War, and was infamous for [[ScaryTeeth filing his teeth to points]] in order to terrify his enemies as he rode across the battlefield [[OffWithHisHead chopping off heads]]. After being run down and killed in the woods on the outskirts of Sleepy Hollow, [[spoiler: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 [[MakesUsEven spares Ichabod]] and his friends and instead [[TheDogBitesBack claims his former master as his final victim]], returning to Hell with a triumphant cry.
25	* MoralEventHorizon:
26	** [[spoiler: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.)]]
27	** [[spoiler:Lady Van Tassel]] crossed the line when she [[DealWithTheDevil 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, [[WouldHurtAChild including their young son]].
28	* {{Narm}}:
29	** 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.
30	** The scene where the Horseman [[spoiler: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 [[BlackComedy film]], it may be intentional.
31	* NarmCharm: Creator/ChristopherWalken as the not-yet-Headless Horseman should be terrifying, but his MessyHair and scream can come of as goofy. Nobody is complaining, though.
32	* NauseaFuel: 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 {{Squick}}ed out.
33	* OneSceneWonder:
34	** Creator/ChristopherWalken 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. Creator/RogerEbert, in his review, refused to give away Walken's casting, but declared it to be "the only logical choice."
35	** Also Creator/ChristopherLee, who shows up in one scene at the beginning as the Burgomaster who orders Ichabod to investigate the killings at Sleepy Hollow.
36	** 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).
37	* QuestionableCasting: Does Creator/ChristopherWalken sound like the first name to come to mind when casting the Headless Horseman? Not for many. But it's ''awesome''.
38	* SpecialEffectFailure: 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 [[spoiler: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.
39	* SpiritualSuccessor:
40	** 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.
41	** Produced by Creator/FrancisFordCoppola, ''Sleepy Hollow'' is, in a sense, a follow-up to Coppola's other two DarkerAndEdgier 90's horror adaptations- ''Film/BramStokersDracula'' (which Coppola directed) and ''Film/MaryShelleysFrankenstein'' (which he produced).
42	* {{Squick}}:
43	** [[spoiler: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]].
44	** The Horseman (with his mouth of POINTED TEETH) does a lip-lock with [[spoiler:Lady Van Tassel]]. This cuts the skin around her mouth open, causing blood to spill out.
45	* StoicWoobie: 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 [[spoiler: when Ichabod suspects Katrina]].
46	* TheyWastedAPerfectlyGoodCharacter: Young Thomas Killian, who could have provided some interesting exposition and gravitas if [[spoiler: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.]]
47	* TheWoobie: Katrina has already lost her mother at the start of the film. [[spoiler: 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!]]

Context YMMV / SleepyHollow1999