We know—this story is hilarious. Then how can it be a tragedy? Hear us out. Irving makes fun of nearly every literary style and genre that he uses, and his use of tragedy is no different. Even though all of the parts of a tragedy are there, Irving changes them around so those in the know will be laughing out loud. Time for you to be in the know.
In a normal tragedy, our protagonist would be a pretty awesome guy or lady. They'd be good looking, smart, moral, probably rich, probably royal, everyone likes 'em… the whole shebang. Ichabod, not so much. He is dirt poor, laughably ugly, greedy, mean, and sniveling. He's basically the opposite of your typical tragic hero.
In this stage of the tragedy plot, the hero is missing something and makes a plan to get it. What is Ichabod missing? Money. He needs money to keep stuffing food in his face, and it's just dawned on him that marrying rich is a good way to keep him knee-deep in Dutch pastries for the rest of his life. So his goal is set: he wants to marry Katrina Van Tassel.
A tragic hero normally has some fatal flaw that leads them down the dark road to destruction. In Ichabod's case, it's not tough to spot. This guy loves to eat, and he wants all of your cool stuff for himself. Greed, not love, leads Ichabod toward Katrina.
Surprisingly, his shtick seems to work. Katrina has eyes for Ichabod, and she ignores her other, more handsome and popular boyfriends. So far, this greed thing is going pretty well for Ichabod.
Things don't stay dreamlike for long. Ichabod refuses to fight Brom for the girl, so Brom decides to make Ichabod's life a living hell. Ichabod doesn't even know that Brom is the one causing trouble; he just knows that things aren't going quite as planned.
Ichabod's greed has finally caught up to him. The player gets played by his lady, who was just using him to make Brom jealous. When her plan works, she dumps the zero and gets with the hero (or villain?). Looks like his greed blinded him to the game that Katrina was playing.
To top it off, Ichabod has to go home alone. We all know he's scared of the dark, and he starts to imagine ghosts and ghouls lurking in the forest. Everything is starting to fall apart, and there's nothing Ichabod can do to make it better.
Now things have really taken a turn for the worse. The Headless Horseman chases after Ichabod and knocks him off of his seat. And that, folks, is the last time we ever see Ichabod. Either the Horseman killed him, or he ran away. Either way, the Ichabod we know is destroyed.
Tragedies often have a catharsis (Greek-speak for a release of emotion or tension) and reveal at the end—and "Sleepy Hollow" is no different. We don't know about you, but this is what we were waiting for. We kind of felt like Ichabod had it coming when the Horseman came after him. The townspeople seem to be okay with his death/disappearance, too. The reveal part comes when we learn that it was Brom, the town prankster, all along… right?