* AlternateCharacterInterpretation: There is a strong recent trend to make Ichabod Crane, not merely the protagonist of the story, but actually an heroic character, while Brom Bones is regarded as at best a JerkJock -- which are both far from Irving's intention to have Bones be the hero and Ichabod a superstitious wimpy moocher. On the other hand, Ichabod seemed more interested in his girlfriend's father's money than his girlfriend, so it's also kinda easy to make him an AssholeVictim.
** The Horseman: a ScoobyDooHoax by Brom Bones used to scare Ichabod away, or a real demonic figure back from the dead to haunt the forest?
*** For that matter, even if it ''was'' Brom, did he really just scare Crane off, or use the locals' belief in the Horseman to get away with a much darker manner of disposing of his rival?
*** At least one adaptation had it both ways: Bones tried to scare off Crane as a fake horseman but gets knocked out in the process, only for ''the real'' Horseman to show up!
** One thing that's rather interesting - Disney actually has it rather faithfully, although [[AdaptationalVillainy playing Brom Bones's villainy up a tad more]], making it seem like TheBadGuyWins. But at the same time, try watching it with an adult perspective. As one Website/YouTube comment puts it:
--> "Me watching it at 10: Oh that jerk! Brom got the girl!"
--> "Me watching it at 20: ...wow...Ichabod is a gold digger."
* NightmareFuel: The ending of the 1999 CGI film "The Night of the Headless Horseman". [[spoiler: Our InUniverse narrator reveals he is Brom Bones, who made a DealWithTheDevil to have the Headless Horseman carry off Ichabod Crane. But, after getting what he wanted, he has to pay back the debt, and so he explains now he has to ''become'' a replacement Headless Horseman. Having said this, he ''pulls his head off his shoulders and lays it on the table'', asking his audience/the viewers to "look after it" while he goes and finds a new one. Cue a close-up of the creepy, UncannyValley decapitated head booming out an EvilLaugh as the final shot of the film.]]