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Ichabod’s lack of self-awareness makes him a comical protagonist and anti-hero. The name Ichabod Crane is intentionally silly and draws a comparison to an awkwardly large bird. Highlighting Ichabod’s awkwardness is his inflated perception, which provides comic relief throughout the story. For example, Ichabod believes his singing voice, education, and appetite for the finer things make him a desirable suitor and intellectually superior to his neighbors. However, the narrator strongly implies that Ichabod is only an average singer, describing his voice as nasally and loud. He also frequently does foolish things, like rigging up a security system for the schoolhouse that Brom easily dismantles. And Ichabod foolishly mistakes disinterest among some of the young women in the community for shyness. Taken all together, Ichabod’s awkward appearance and embarrassing behavior are hilariously at odds with his self-perception.

Additionally, Ichabod’s belief in and fear of the supernatural exposes him as an intellectual fraud. Thus, far from appearing high-class and dignified, Ichabod often looks silly or ridiculous. The detail that his favorite author is Cotton Mather especially highlights Ichabod’s overblown perception of himself as an intellectual. In fact, Cotton Mather was well known for ruining his own intellectual legacy by persecuting innocent people during the Salem Witch Trials. Moreover, Ichabod fills the sizable gaps in his knowledge with a belief in the supernatural. Anything he does not understand, he fears. Ichabod’s fear of the unknown is symbolized by his fear of the dark, which plays a significant role during his midnight run with the Headless Horseman. In the end, Ichabod’s shame at falling for Brom’s prank shows that he has finally attained some self-awareness. Even then, rather than face the fact, he runs from it and from Sleepy Hollow, never to return. Therefore, Ichabod’s inability to face up to his mistakes is a final indictment on his character.

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