Story Playlist 5: The Legend of Sleepy Hollow

Washington Irving: “The Legend of Sleepy Hollow” (1820) Washington Irving’s marvelously spooky tale of revenge, set in early New England, is the best-written story I’ve encountered in the first week of my short story project, and yet it is the earliest. Poe and Hawthorne are fine writers, but seem both stuffy and over-stuffed, like pillows with too much goose-down inside, what with their murderer’s row of adjectives and contorted word orders. Sure, that was high literature during their time, but reading it now feels old-fashioned in a way that Irving (and Ambrose Bierce) do not. Irving’s story predates Hawthorne and Poe, but feels fresher. It would not seem out of place in a contemporary lit journal. The balance of humor to action to description is just right, making Irving a truly timeless author.

His story has also haunted readers since its publication, and has inspired countless variations. Ichabod Crane is an awkward, gangly school-master in a rural Dutch settlement of 18th century New England (specifically in what was once North Tarrytown, NY, and which renamed itself Sleepy Hollow, NY). Despite his physical oddness, Crane has a way with the ladies, and his eye falls on Katrina van Tassel, the Rubenesque daughter of a local wealthy farmer. Vying for Katrina’s affections is the local macho male, Brom Bones (if this were set in the 1990s, Brom would be captain of the football team and destined for fraternity fame). Brom and his gang of lads toy with Crane, but there’s a real feeling of competition for Katrina. Ichabod teaches Katrina singing, and therefore has an “in.” He also has a vivid imagination, and gets the jitters on his trips home from dinner and fireside stories at the homes of the locals.

Crane receives an invitation to a big party the whole community will attend. At the party, Katrina seems to favor Crane over Brom’s muscled and manly courtship display, and the skinny, turkey-necked Crane looks to have won her hand. As the party winds down, several guests, including Brom, tell of their encounters with the Headless Horseman, the ghost of a Hessian mercenary whose head was blown off by a cannonball during the Revolutionary War, and who was buried in the local graveyard. By night he roams the lonesome forest roads, returning each morning to his grave. In true alpha-male fashion, Brom claims that he raced the Headless Horseman, and was winning too, when he crossed a covered bridge near town, at which point the Horseman disappeared.

With these stories planted in Crane’s percolating imagination, the party disperses, and Crane heads home. Along the dark road he wonders if his mind is toying with him, as he hears strange sounds and fears he is being followed. Turns out he is. The Headless Horseman comes charging out of the woods and begins to chase him. As Crane flees, he recalls Brom’s experience of having escaped the Horseman by crossing the bridge into town. If only he can reach it, he might just escape. Crane gallops to the bridge and crosses it. He looks back to the Horseman, reared up at the far end of the bridge. But the Horseman lifts his severed head, which he has carried by his side, and hurls it across the bridge at Crane.

The next morning, Crane is nowhere to be found. But on the town side of the bridge there is a shattered pumpkin. Brom goes on to marry Katrina van Tassel and, as Irving notes, “was observed to look exceedingly knowing whenever the story of Ichabod was related, and always burst into a hearty laugh at the mention of the pumpkin, which led some to suspect that he know more about the matter than he chose to tell.”

Irving leaves us with a proto-Scooby Doo mystery. Is the Headless Horseman real, as many in Sleepy Hollow believe? Or did Brom Bones decide to do away with his rival and embody the legend himself, posing as the Horseman in order to dispose of Ichabod Crane? Such question-mark endings are popular in more recent fiction and film, stories in which it is up to the reader to determine whether something supernatural has taken place, or whether the supernatural appearance is a cloak to cover over natural means and motivations.

Unlike Scooby Doo, Irving doesn’t feel the need to spell out the ending, openly unmasking the culprit behind the supernatural occurrence. His rhetorical means of implicating Brams is a bit more subtle. By the same token, he doesn’t completely disabuse readers who want a supernatural experience, by providing an authorial explanation. A clear-cut ending allows you to close the book and consider the case closed along with it. You can get on with the next text on your list, or consider what groceries you need to pick up the next day. Stories like “The Legend of Sleepy Hollow” refuse to allow this, prompting you to hold off on that next book, and lie in bed with the lights out, wondering whether the Horseman was Brom Bones or the ghost of a headless Hessian. Irving’s “Sleepy Hollow” lets the reader eat his cake and digest it too, giving a lesson in the value of hints over statements.