Character sheet for Washington Irving's classic short story The Legend of Sleepy Hollow.
- Anti-Hero: Despite displaying a number of positive traits, the story focuses largely on his flaws; envy, avarice, gluttony, and sloth.
- Asshole Victim: Maybe. If you subscribe to the "killed by the Horseman" ending, he had it coming.
- Big Eater: He has a huge appetite in spite of his rail thin physique.
- Did Not Get the Girl: He attempts to win the hand of Katrina in marriage to get access to her father's vast wealth, but he fails and leaves dejected.
- Hot for Student: 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.
- Jerkass: Ichabod gets less and less appealing as the story goes on, peaking when he thinks of how, once he's married Katrina and acquired her father's great wealth, he'll tell everyone he associated with as a schoolteacher to screw off.
- Meaningful Name: "Ichabod" is traditionally translated as "Inglorious," while "Crane" hints at the schoolmaster's tall, thin frame and beaky nose.
- Never Found the Body: The story leaves it ambiguous whether the Horseman killed Crane or simply scared him away from Sleepy Hollow.
- Noodle Incident: 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.
- Rounded Character: Although his most-obvious trait is his Greed, Ichabod is actually a rather multi-faceted character. Beyond his selfish ambitions, Ichabod is also superstitious, imaginative, has a (typically unhealthy) sense of curiosity, and even has some positive traits thrown in for good measure.
Abraham "Brom Bones" Van Brunt
Sleepy Hollow's local hero and Ichabod's rival.
- Anti-Villain: Brom Bones is depicted as displaying all the qualities of a Great American Hero: bravery, recklessness, and square-jawed, good ol' boy charm. He was also pretty jealous of Ichabod as he once bragged to his Sleepy Hollow Boys, "I'll double that school master up and lay him on a shelf of his own schoolhouse!" Ichabod was too clever to get into a scrap with Bones. 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.
- Offscreen Moment of Awesome: 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.
Katrina Van Tessel
The love interest of both Ichabod and Brom Bones.
- Operation: Jealousy: Katrina uses Ichabod to pull this on Brom.
- Satellite Love Interest: She isn't given much characterization other than being the object of affection for Ichabod and Brom.
The Headless Horseman
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.
- Big Bad: The main villain of the story, for what little role he has in it anyway.
- Breakout Villain: The Horseman only had a very brief scene in the already short story just near the end, and it's implied that it might not even be a real ghost. In spite of this, the sheer mystique and inherent scariness behind the character ended up making it a horror icon on par with Dracula and Frankenstein, with numerous movie adaptations and modern day takes on the character coming out in the years since Washington Irving's story was published.
- Cannot Cross Running Water: 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.
- Flat Character: 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.
- Headless Horseman: The Trope Codifier. 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.
- Hellish Horse: His horse is described as having a powerful frame which, combined with the silhouette of the horseman atop, looks like a "gigantic monster ready to spring upon the traveler", even before Ichabod realizes its rider is headless.
- Holy Burns Evil: 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 workthe horseman throws his pumpkin head at Ichabod and gallops off past him unharmed.
- Maybe Magic, Maybe Mundane: The story makes it ambiguous whether the apparation is real or is just Brom Bones playing a trick on Ichabod.
- Off with His Head!: He's given some backstory; he's believed to be the ghost of a Hessian trooper that had his head shot off by a stray cannonball during "some nameless battle" of the American Revolutionary War, and who "rides forth to the scene of battle in nightly quest of his head".
- Pumpkin Person: The horseman carries a pumpkin head by his side, which he throws at Ichabod in the end.
- The Voiceless: Has no dialogue at all. Justified, as he's headless.