** Is Brom Bones a vindictive bully who played a nasty trick on a harmless, lovestruck nerd, or a down-home, all-American good ol' boy who gave just desserts to a venal, manipulative coward? There is a strong modern trend to make Ichabod Crane be actually a 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 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?
** Some food for thought here on both sides of the argument. Earlier in the text it is said the Horseman is riding looking for his head. Meaning he doesn't have a head. When Ichabod sees the Horseman he believes he is carrying a head that he throws at him. Afterwards a smashed pumpkin is found -- all of this seems to indicate Brom dressed as the Horseman to scare Ichabod off.
*** However let's also remember something here, the Headless Horseman has no head, meaning he has no eyes. He certainly can't see too well if he was real. The pumpkin is seemingly used as a projectile, which it succeeds in getting Ichabod off his horse. This is a pretty good soldier-like move, something the Horseman was. And after all, his own head was taken off by a projectile!
** Also due note when we hear about Ichabod in New York, he has picked up a lot of ambition since leaving Sleepy Hollow. All throughout the story Ichabod is very much more a laidback guy going from house to house seemingly content with his lifestyle. He even has an excuse as to why he moved which seems a bit convenient. As perhaps New York Ichabod isn't Ichabod as he once was.
*** 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 [[MurderTheHypotenuse a much darker manner of disposing of his rival]]?
*** Maybe he did not want blood on his hands.
*** 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. Watch Doug Walker's Disneycember video on the movie to learn why.
** An actual canon case of this is in the 1999 CGI film "The Night of the Headless Horseman"; here, Katrina, usually depicted as more or less an innocent caught up in the LoveTriangle, is quite blatantly revealed to be egging on both Brom and Ichabod for her own amusement, waiting to see who will ultimately prove worth keeping.
** Depending on your interpretation of Ichabod's motives, combined with ValuesDissonance: Is Ichabod kind of a creepy old lecher who is trying to butter up a ''teenager'' in order to marry her for her father's wealth? Did he [[AssholeVictim have it coming]]? This of course depends also on the adaptation, where age differences might be less pronounced and the characters portrayed in more and less sympathetic lights.
* HilariousInHindsight: Mr. Irving at times admits he made stuff up, such as admitting his inspiration from older tales mixed into the new world. But oddly enough there are several eerie coincidences that have been uncovered that could make it seem like there was more to this story than fiction but it's more likely they are [[AccidentallyCorrectWriting nothing but hilarious coincidences]].
** The most astonishing being that a revolutionary war battle record did indicate the death of a solider and his horse via canon fire. And if they had been given a group burial they would have been buried very close to where the fictional Horseman rides out from. While many towns have always had their ghost stories, there's little evidence at all that this actual event had influence on Irving or was linked to any purported haunting before this tale was told. While many smaller pieces are found among many war battle records, the fact there was one all combined close to North Tarrytown/Sleepy Hollow is just astonishing.
* 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.]]
* OneSceneWonder: The story isn't even 30 pages long, and Ichabod's entire encounter with the Horseman only lasts ''1 and a half pages''--but its also the most memorable part of the whole tale.
* SignatureScene: The climatic chase scene is by far the most famous part of the story.
* ValuesDissonance: A modern reader would likely find Ichabod and Brom both equally unsympathetic. Ichabod's essentially a sneering, self-important, arrogant, mooching gold digger, and Brom Bones is a thuggish, anti-intellectual bully. Throw in the hints that Katrina was just manipulating both of them, and you could very well end up with DarknessInducedAudienceApathy.
** Judging by the alternate character interpretation example above, modern readers see Brom Bones a WellIntentionedExtremist. Especially if the theory of him posing as The Headless Horseman is true.