"The Legend of Sleepy Hollow" by Washington Irving is an American classic. Many adults had grown up with it. But the importance of Irving's work goes beyond nostalgia. This short story speaks about an early American Republic, of the unpleasantness that came with a shift from English colony to independent country.
"The Legend of Sleepy Hollow" reveals something of the malaise the author felt about the bustling, industrious society that America was becoming. In the classic showdown between Ichabod Crane and Brom Bones, Irving sketched an American crossroads, a choice between the goblin-haunted, past-driven schoolteacher and the brash, up-and-coming, muscular realist—which one will win the girl?
Sleepy Hollow itself is presented as a sort of refuge from the bustling America, a haven where "romance" is still possible.
Ichabod Crane, the famous schoolteacher, functions as artist in Irving's scheme. Crane is shown in unflattering colors—as a grotesque figure, ravenous in his hunger for material success.
Yet he is also characterized as "our man of letters," as "traveling gazette" for Sleepy Hollow, which unmistakably casts him as a writer, even as an intellectual.
Ichabod, on the otherhand, is also a storyteller, but of the Cotton Mather school; i.e., of the past stories of witches and demons. This marks him as backwards-looking. Ichabod's challenge, as Irving articulates it in "Wild West" fashion, is: Can he establish himself? Marry Katrina? Defeat his rival?
Brom Bones, Ichabod's rival, has a cultural interest of his own, given the dynamics of early American culture. Rowdy, strong, brash, and fearless, Brom Bones personifies a figure who will challenge all manners and religious rigor. Bones is also the man who fights phantoms and boasts of encountering the infamous, legendary Headless Horseman.
In Irving's showdown, the two males battle it out by replaying a scene of legend. But Bones is able to best Ichabod by taking charge of the event, by scripting it so perfectly that he becomes the artist, impersonates the Horseman, substitutes a pumpkin for a head, and routs his rival. A new era is at hand, and we see the classic exchange: Ichabod Crane disappears from the scene, but the legend of his encounter with the "ghost" is born.