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Headscratchers / Sleepy Hollow (1999)

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  • How can Lady van Tassel inherit all of the van Tassel and van Garrett lands after Katrina dies if she already faked her own death? Kinda hard to show up in probate court and stake your claim to your husband's estate after they've already interred your corpse next to his.
    • She could just say it was a case of mistaken identity. The only people to whom the scar on the hand meant anything were Katrina and Crane, and Lady van Tassel was already working on that. Once the people who could raise a fuss were out of the picture, she'd show up, say she panicked and fled into the woods or something, and receive her inheritance.
      • It was 1799; neither the telegraph nor the telephone was invented yet. So news of her death or faking her death, wouldn't be out until it was sent by snail mail. As far as the nearest major city was concerned Lady Van Tassel was still alive.
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    • She could use essentially the same line she gave to Katrina. "Your father saw the horseman approach me with his sword unsheathed" - she doesn't have to 'know' why the horseman didn't attack her. Or she can say she fled and got lost in the woods, only to arrive in town and 'discover' her husband and stepdaughter dead. As for the existing body, the servant girl Sarah would be unaccounted for.
      • The original script had a line that covers this inconsistency: in her Motive Rant to Katrina, Lady van Tassell tells her that: "Tomorrow I'll totter out of the woods and spin a tale how I found Baltus and Sarah in the act of I watched, the Horseman was upon them, and off went Sarah's head! I fainted and remember nothing more..."
  • Here's a better one: What did Lady van Tassel expect to do with all of the van Tassel and Van Garret lands given that the population of Sleepy Hollow was abandoning the area like rats leaving a sinking ship? Step 1: raise Headless Horseman from the dead to kill all her rival heirs And Then What?
    • This was back in the day when land = power. And also wealth. If Lady van Tassel's scheme had gone to plan she would've had a lot of land held in her name. She could take all the land and turn it into a plantation. Or maybe since she was a Wiccan she had some sort of mumbo-jumbo "one with the land" philosophy. Force everyone off the land and then on it.
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    • Or she could have sold it all for a nice profit (since if the police men at the beginning are anything to go by, the only ones really buying into the superstition are the people who live in Sleepy Hollow, so she could have always sold it to someone not from the area). Since to this troper, so much of her bitterness seemed to be because she grew up poor so even selling the land would have entitled her to a very comfortable life.
    • She wasn't exactly sane. She may have simply wanted to one-up the Van Garretts and Van Tassels by owning all their lands.
    • She couldn't actually do anything, widowed women couldn't legally do anything with property (such as sell or lease it) until over 50 years later, It would be legally still her husbands (weird will stuff) until she remarried. I think it was mainly oneupping the families who had buggered her over.
      • She was still an attractive woman for her age and had already seduced at least one man beside her husband, plus she could have had some kind of witchery to fall back on; she could have been planning to take a new, pliable husband and manipulate him to achieve whatever her goal was (sell the land and be rich, live on it comfortably and undisturbed, ect).
  • When Brom and Ichabod fight the Horseman, the Horseman seems disinterested until they run away, and which point he drops down from the other side of the bridge to continue the fight. Why would he bother to stop them from leaving him alone if that's what he wanted in the first place?
    • I think Brom pissed him off a little too far.
    • Maybe the Horseman decided that Brom probably wasn't going to ever leave him alone, and that if he didn't kill him he could look forward to being shot every time he rode into town. Not a major problem, but definitely an inconvenience.
    • Also, the Horseman probably found he was enjoying himself. An opponent who could fight back, for the first time in a long time, had to make a nice change from being forced to kill terrified civilians. The man used to be a professional soldier, after all.
  • Why does Lady Van Tassel look so much older than she should? During her motive rant she claims that Katrina was already born when she and her family were kicked out of their home. She couldn't have been more than 10 in the flashbacks, and yet Miranda Richardson is 22 years older than Christina Ricci, and it shows in the movie. Even if Katrina is supposed to still be in her late teens, Lady Van Tassel should be in her early thirties, at most.
    • I dunno, premature aging due to a rough upbringing? Maybe the dark arts take a physical toll on the body? Remember, her sister didn't exactly look minty fresh when Ichabod met her.
    • Lady Van Tassel only says her family was kicked out on favor of Baltus and his girl child. This does is not clear evidence that Katrina was actually born at the time Van Garret gave the land to Baltus.
    • Keep in mind is in 1799, people grew old faster back then.
    • Lady Van Tassel also had to wait until she was old enough to be considered marriage material for Baltus.
  • Why did Lady Van Tassel kill the servant girl herself and blame the horseman when she could have summoned the horseman to do the deed? It's not like the horseman would only kill the people who could expose her or get in her way. He killed anyone she summoned him for.
    • What Lady Van Tassel needed at that point was a body that no one knew was dead that she could use to stand in for her. In essence, she needed to kill someone quietly and on the down-low, and keep it secret and subtle in order to serve her purposes. She didn't want anyone to know Sarah was dead. If there is one thing the Horseman is not, however, it is secretive and subtle. Sic the Horseman on Sarah, and he'd hunt her down with a lot of noise and drama, and butcher her without caring where they ended up or whether anyone was around to watch him do it. Making the Horseman kill Sarah meant risking that someone would see him do it or would discover Sarah's body before Lady Van Tassel had a chance to make people think that it was her. So the best way to make sure that Sarah died without anyone knowing until it suited her was to do it herself.
  • Why did Jonathan Masbath run INTO the Western Woods after the Horseman destroyed his guard-tower?
    • Because he's panicking and has an invulnerable demon-horseman from the depths of Hell intend on chopping his head off right behind him. He's basically not thinking very far beyond RUN AWAY RUN AWAY FAST.
  • Why did a witchcraft-loathing reverend like Ichabod's father marry a witch in the first place?
    • And why did she agree to marry him?
      • 1) Maybe it was purely lust on his part. Or 2) maybe he used to be different. Maybe he used to be kind and tolerant and open-minded but then something happened that caused his change into the tyrant Ichabod knew. Or, calling back to 1, maybe he blackmailed her. "Give up your sinful ways and marry me to prove that you have renounced Satan, or I'll have you hanged." He found out she had not renounced, so.
      • It's also possible that he didn't know she was a witch before they married and only learned this when he saw her showing Ichabod "magic," though even then (according to the flashback) he only had her executed after he saw Ichabod's copies of her drawings. So he might not have known she was a witch/pagan beforehand, or maybe he felt he had to take action once he saw that she was influencing Ichabod with 'soul-endangering' practices.
      • As for why she agreed to marry him, she might not have had a huge amount of choice in the matter. As anyone who's read Pride and Prejudice will tell you, marrying for love was something of a luxury around that time, especially if you were a woman in a society where women had very few rights or opportunities otherwise. He's a respectable, influential and apparently rather prosperous member of the community who will be able to give her what, for the late eighteenth century, appears to be a fairly good life on the surface. She might not have been in a position to turn him down.
  • Why does Lady van Tassel need to kill everyone who knew about Winship's pregnancy and van Garrett's new will? Just kill Winship with her child, and van Garrett's will lapses. The will becomes irrelevant, so why the need to kill everyone who knows about it? It can't be to cover the whole thing up, because once she takes the whole estate after Baltus and Katrina are dead, suspicion would probably fall on her anyway.
    • Possibly if it was revealed that the will allowed the land to pass to Winship and her child, and just they died, then it would go to their next of kin instead.
    • Remember that before Ichabod arrives on the scene, people don't know it's a murder plot. They just think it's a demon going around killing at random. No one would ever suspect Lady Van Tassel because they're superstitious small town folk who don't rationalise why the Horseman is coming. As far as they know, the people the Horseman kills are just random.
  • So... in the end, Ichabod, Katrina and Young Masbath return to New York, and all is well. Except that the case is still unsolved, as far as the New York City Police is concerned. Ichabod might be a skeptic no more, but the burgomaster doesn't seem like someone who'd believe a story about headless ghosts running amok in town. What's more, Ichabod doesn't have any evidence left since both the horseman and Lady van Tassel have disappeared, presumably forever. What's even more, he got tangled in all of this mess by falling in love with a potential suspect, thus compromising his neutrality. The burgomaster said that this was his last chance to redeem himself, and it looks like he blew it, albeit unintentionally. All in all, this doesn't seem like a very happy ending to me.
    • Well, if we're entirely honest Ichabod doesn't seem to have been entirely happy or have completely fitted in as a policeman, and if nothing else Katrina has inherited all of her father's wealth, so is presumably loaded.
    • Also, what evidence do we have that Crane needs to tell his superiors about his relationship with Katrina? He could easily say that she and Masbeth are initially there to testify in his favour and confirm that he did catch the killer but was forced to kill them in self-defence (particularly when he'd have at least a few hours to come up with a convincing story that doesn't include headless horsemen and witches), and then let it appear that things between him and Katrina grew closer while she was dealing with the relevant paperwork regarding her father's estate.
    • Heck, all they really need is a carefully edited version of what actually occurred: Lady Van Tassel was behind the murders, and in league with an (unidentified) assassin who committed them on her orders so that she could secure the Van Tassel estate and avenge herself on the men she believed ruined her family. When she was discovered and facing exposure, she fled into the woods, and although her body was not found evidence was discovered that her employee double-crossed and killed her. They just need to leave out the part where the assassin was an undead headless horseman summoned from the blackest pits of Hell. There's plenty of proof to support Lady Van Tassel's guilt (the beauty of the film is that once you get past the fact that the murderer is a headless horseman, it's actually pretty much just a murder mystery) and it's not like there's anyone else who can really challenge the version of events our heroes put forward.
    • Besides, recall that the start of the movie shows that the level of policework at the time is "Dead body in the river, huh? Well, throw it out before it stinks up the place." Maintaining steadfast neutrality or avoiding the appearance of favoritism was likely not something they gave much of a flip about. "Crane married an important witness in his case, eh? Well, good, maybe having a woman will settle that yammering fool down."
  • How much did the sister know? It did not seem like she approved with the revenge plan but fear of being implicated herself, or misplaced loyalty, may have kept her from coming forward with the name of the culprit. There seem to be a lot of unanswered questions behind her story.
    • It's possible she didn't know specifics. She may have known that the Horseman was being summoned by someone who had his head, but not who that person was.
    • She doesn't know. If she did, she would have told Ichabod "my sister is summoning him" and she wouldn't have to invoke an all-knowing spirit to give Ichabod clues. She says "when the other comes, I will hold him". That's referring to the spirit she's summoning to give the answers. The spirit knows and she doesn't; it's just using her as a vessel to tell Ichabod.
  • When Jonathan Masbath's body is discovered, Ichabod Crane ask another character: "You have moved the body?", and the other character answers: "I did." But Crane's subsequent deductions depend on the body being at the exact same place where it was killed! His reconstruction of the murder ("The attacker rode Masbath down, turned his horse, came back to claim the head") are based on the position of the body relative to the hoof prints. He sprinkles some powder over the area just in front of the severed neck. But there is nothing particular about this area because the body has been moved! Why would he act like this if he knew that the body was not at the same place? And in these conditions, why are his deductions correct?

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