History Characters / TheLegendOfSleepyHollow

** Leading Crane on and then denying him lead the schoolteacher to leave the party they were attending early and thus his fateful encounter with the Horseman.

[[caption:right:width:350:As he appears in ''WesternAnimation/TheAdventuresOfIchabodAndMrToad'']]

* HotForStudent: Ichabod gives Katrina psalmody lessons. She's eighteen, though, and also this was considered a much more mature age, one far more ready for marriage at the time the story is set.
* GoldDigger: A rare male example. Ichabod wants to get with Katrina in no small part due to her father's money.

* CannotCrossRunningWater: Brom claims this is how he beat the Horseman in a race--it can't cross over the church bridge adjacent to the Old Dutch Burying Ground. This turns out to be false in the end, as the Horseman is described as having passed by Ichabod after throwing the pumpkin head at him, meaning he probably did cross the bridge unharmed.
* FlatCharacter: The Headless Horseman is frightening, but it isn't really given any characterization beyond "Scary Headless ghost who chases Ichabod on horseback". Justified, as its appearance may or may not have been a ruse cooked up by Brom Bones to scare off Ichabod. The closest personality trait assigned to it is as being an "arrant jockey" when Brom tells his story of racing the horseman, but this encounter may or may not just be a story he made up. Ironically, this ends up adding to the mystique and terror behind the character.

* HeadlessHorseman: The TropeCodifier. While far from the first appearance of this kind of character (with appearances of headless horseman dating back to European Folklore of the Middle Ages) it is definetely the most iconic.

* HolyBurnsEvil: Subverted. Brom's story claims the Horseman can't cross the Church bridge, and that he bolted and vanished in a flash of fire. Ichabod exploits this by running across the bridge. It doesn't work—the horseman throws his pumpkin head at Ichabod and gallops off past him unharmed.

* TheSpeechless: Has no dialogue at all. Justified, as he's headless.

* AdaptationalNiceGuy: In contrast with the original story as detailed below, Ichabod is often portrayed in adaptations of the story as far more noble, kind, and heroic.

* AssholeVictim: Maybe. If you subscribe to the [[AmbiguousEnding "killed by the Horseman" ending,]] he had it coming. Downplayed with the alternative ending, as he still deserved to be chased out of town.

* GoldDigger: Rare male example. Ichabod wants to get with Katrina in no small part due to her father's money.

!!Katrina Van Tessel

!!Ichabod Crane

!!Abraham "Brom Bones" Van Brunt

!!The Headless Horseman

* TheSpeechless: Has no dialogue at all. Justified, as he's headless.

* AdaptationalNiceGuy: In contrast with the original story as detailed below, Icabod is often protrayed in adaptations of the story as far more noble, kind, and heroic.

* NoodleIncident: Whatever happened with his final encounter with Katrina. It's not known what was said, but it's pretty clear she rejected him as he left the Van Tassel farm in a huff.

* UncertainDoom: One of the biggest mysteries about the story is what became of the old schoolteacher: was he killed and dragged off to the afterlife by the Headless Horseman or simply scared out of town never to return.

* AdaptationalVillainy: Most stories based on the story often have Icabod as the hero, thus as his rival Van Brunt is often protrayed as more villainous.

* AssholeVictim: Maybe. If you subscribe to the [[AmbiguousEnding "killed by the Horseman" ending,]] he had it coming.

Character sheet for Washington Irving's classic short story ''The Legend of Sleepy Hollow''.

The love interest of both Ichabod and Brom Bones.

* FlatCharacter: She's given little charactization beyond being the third corner in a LoveTriangle with Crane and Van Brunt. Most stories based on ''Sleepy Hollow'' expand her character but will almost always have her as Crane's LoveInterest.

* UnwittingInstigatorOfDoom: Her role depends on the how you interpete the endig due to her attempt to [[OperationJealousy use Crane to make Abraham jealous]].

* TheVoiceless: Has no dialogue at all. Justified, as he's headless.

* AdaptationalVillainry: Most stories based on the story often have Icabod as the hero, thus as his rival Van Brunt is often protrayed as more villainous.

The villain of the story. He is apparently the ghost of a Hessian trooper who lost his head in a battle in the American Revolutionary War, and rises from the grave in search for his head.

* AntiVillain: Brom Bones is depicted as displaying all the qualities of a Great American Hero: bravery, recklessness, and square-jawed, good ol' boy charm. As such, even though the entire story (in one interpretation) hinges on the consequences of a prank he pulls, the reader never loses sympathy with him.

* OffscreenMomentOfAwesome: He tells a story of how he raced the Headless Horseman one night for a bowl of punch and ''won''. He claims that he didn't even anticipate that he would win and that it was simply luck that the Horseman couldn't cross the covered bridge.

* FlatCharacter: He isn't given much, if any, characterization in the original story. Its justified because its appearance may or may not have been a ruse cooked up by Brom Bones to scare off Ichabod. The closest trait assigned to him is being an "Arrant Jockey" by Brom. Ironically, this ends up adding to the mystique and terror behind the character.

* OffscreenMomentOfAwesome: He tells a story of how he raced the Headless Horseman one night for a bowl of punch and ''won''.

* HeadlessHorseman: The TropeCodifier.

* CannotCrossRunningWater: Brom claims this is how he beat the Horseman in a race--it can't cross over the church bridge. This turns out to be false in the end, as the Horseman is described as having passed by Ichabod after throwing the pumpkin head at him, meaning he probably did cross the bridge unharmed.