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1* AdaptationDisplacement:
2** Given how long it took for this movie to be released on home media, there are multiple generations of people that are more familiar with Mr. Toad's Wild Ride, the popular Ride/DisneyThemeParks attraction, than they are with the Wind in the Willow segment it was based on.
3** "Sleepy Hollow" has a fair number of fans who at least remember parts of it from numerous "Disney Halloween" specials in TheEighties and [[TheNineties early 90s]], but may never have actually seen the whole movie (or at least the second half).
4* AlternativeCharacterInterpretation:
5** Ichabod. He's the protagonist of the story, but he also comes off as manipulative {{Jerkass}}. Whether he's a "good guy" and how sympathetic he is varies among the viewer. In fact, Disney [[ShownTheirWork sort of gets one thing right here]] - the original tale is open to as much AlternativeCharacterInterpretation as the AnimatedAdaptation.
6** Also Katrina and Brom. Is she honestly flattered by Ichabod, or is she just playing with him, perhaps using him to make her other suitors jealous? And is Brom just a bully, or is he honestly in love and wants to protect her from a gold digger? The original tale is also ambiguous about them in this way.
7*** Also regarding Katrina, does she really just flirt for the fun of it or is she doing this for being very much aware that most guys may want her just because she's rich?
8*** Furthermore. Is there an actual LoveTriangle? Or is Katrina feigning interest in Ichabod to bring Brom down a few pegs?
9** Is the Horseman real? Disney started a pretty common trend of adaptations that lean on the "yes" column when the book leaned "no", but most of the hints from the original are still intact. The most difficult moment is when Ichabod looks down the neck, but you could still ''maybe'' assume he was panicking and the rider was keeping their head covered while inside the armor; it's already suggested in the leadup to the Horseman's appearance that Ichabod's overwhelming fear is messing with his perception of things.
10*** The Walt Disney Company's official stance as of 2023 seems to be "yes", as the ''[[WesternAnimation/OnceUponaStudio Once Upon a Studio]]'' short has Brom and the Horseman appear as separate characters. However, since this short was made without Creator/WaltDisney or any of the staff who made this film, it may be different from what they had intended.
11** Assuming the Horseman is real, is he a TragicMonster condemned to roam the Earth until he finds his lost head ? Or maybe he's a malevolent ghost who was evil even as a human ? It's quite hard to tell considering he's the less fully explored character of all.
12* BigLippedAlligatorMoment: A brief moment in the Headless Horseman song is a creepy old guy sitting down to deliver the line "And some don't even wear their skin!" He is never seen before or after that moment.
13%%* CreepyAwesome: The Headless Horseman.
14* EnsembleDarkhorse:
15** Katrina Van Tassel has a small fan following; she has some fanart and it helps that she is a MsFanservice.
16** Tilda has also gotten a following over the years who see her as an endearing character who is [[BigBeautifulWoman more attractive than the movie would indicate.]]
17%%* EvilIsCool: Again, The Headless Horseman.
18* SugarWiki/HeReallyCanAct: Billy Bletcher provided the voice for some memorable Disney villains like [[WesternAnimation/{{Pete}} Pete]] and [[WesternAnimation/TheThreeLittlePigs the Big Bad Wolf]] which while not without their sinister moments they were relative comical and funny. Here he's the Headless Horseman's terrifying laugh. It's his only line of dialogue and it's extremely frightening.
19* HilariousInHindsight:
20** [[AwesomeEgo No one owns like Gaston]]! [[NotSoHarmlessVillain Changes tone like Gaston]]! [[MemeticMutation No one weirdly resembles Brom Bones]] like [[WesternAnimation/BeautyAndTheBeast Gaston]]! Although Gaston is far more of a jerk than Brom.
21** The "Don't even wear their skin" guy [[WesternAnimation/{{Ratatouille}} looks rather familar]]. [[WildMassGuessing Perhaps he's an ancestor of Anton's family who moved to America?]]
22** In the opening narration, the narrator suggests Myth/RobinHood, Myth/KingArthur, [[Literature/VanityFair Becky Sharp]], Literature/SherlockHolmes and Literature/OliverTwist as the "most fabulous characters in English literature". Since then, Disney has made adaptations of the [[WesternAnimation/RobinHood1973 first]], the [[WesternAnimation/TheSwordInTheStone second]] and the [[WesternAnimation/OliverAndCompany last one]], two of which were {{Anthropomorphic Animal Adaptation}}s. The intro to the Sleepy Hollow segment also references Davy Crockett (who had a live action TV series from Disney), Myth/PaulBunyan (who had a short released in the late 1950s), and UsefulNotes/JohnnyAppleseed (who Disney already tackled [[WesternAnimation/MelodyTime the previous film]]).
23*** Although ''WesternAnimation/TheGreatMouseDetective'' does have elements of Sherlock Holmes, and even has a cameo of said character and Watson, albeit in shadow.
24* HollywoodHomely: Tilda in the Sleepy Hollow segment is treated as an AbhorrentAdmirer, but she's generally considered by the film's fans to be [[BigBeautifulWoman attractive in her own way]].
25* JerkassWoobie: Brom Bones, seeing that he's the only one character in ''Sleepy Hollow'' who actually suffers some damages and injures. Not only that, despite his bully tendencies, his EstablishingCharacterMoment and seeing how Ichabod only wanted to marry Katrina for money and free food, show that Brom Bones has some fairly good qualities that make you feel some sympathy for him.
26%%** Mr. Toad after he's thrown in jail.
27* JustHereForGodzilla: Some people watch the film solely for the ''Sleepy Hollow'' half, or even more specifically for Ichabod's encounter with the Headless Horseman. It helps that much of the film's promotional material, including its original poster and 21st century home video artwork, is primarily focused on the ''Sleepy Hollow'' half over the ''Wind and the Willows'' half.
28* OneSceneWonder:
29** The creepy-looking man who says "And some don't even wear their skin!" during the Headless Horseman song has just a few seconds of screentime, but still manages to be extremely memorable.
30** And of course the entire sequence of the Headless Horseman. It happens just at the movie's climax but it's still well remembered nowadays.
31* SignatureScene: The Headless Horseman's introduction is one of the first things that come to mind in the compilation movie thanks to it's buildup, and execution. It helps that the Headless Horseman himself is played completely straight in terms of how [[NightmareFuel terrifying]] he is.
32* SoOkayItsAverage: The public's reaction to the film at the time, though [[VindicatedByHistory it became somewhat more popular as time went on]].
33* TearJerker:
34** The part where Toad, locked in his prison cell, silently cries blaming himself for the trouble he's got into it and vowing to never let his manias get the best of him again.
35** Also, Rat and Mole praying for Toad during their Christmas dinner.
36---> '''Mole:''' ''(sheds a SingleTear)'' And may he get time off for good behavior...
37** During the Halloween party, Brom sees the only other person who's not dancing is Tilda, the short chubby lady who usually follows after Ichabod. She's sitting by herself, clearly dejected that she doesn't have a dance partner, but looks hopeful when she sees Brom looking at her. [[KickTheDog Brom responds by cringing in disgust]], and Tilda looks incredibly hurt.

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