The narrator/author responds to critics who note that he has never written a moral tale (Poe, after all, despised didacticism). So, the narrator tells the story of Toby Dammit, a man of many vices prone to rhetorical bets introduced with the idiomatic, "I'll bet the devil my head..." One day, he and his companion come across a covered bridge with a turnstile in the middle. Dammit, looking for some fun, bets the devil his head that he can jump clear over that turnstile.
He insisted upon leaping the stile, and said he could cut a pigeon-wing over it in the air. Now this, conscientiously speaking, I did not think he could do... I therefore told him, in so many words, that he was a braggadocio, and could not do what he said. For this I had reason to be sorry afterward;—for he straightway offered to bet the Devil his head that he could.Right on cue, a mysterious stranger arrests their attention when he clears his throat. He decides to take Dammit up on his bet — to the dismay of the narrator, who notes, "I don't care who the devil he is." Misgivings of his friend aside, Dammit gracefully jumps over the turnstile — though as he reaches the apex of his leap, things change: his body makes it over, but his head does not ("what might be claimed a serious injury," the narrator notes). The mysterious gentleman claims the head and walks off. It turns out that, directly above the turnstile, was a thin, razor-sharp metal bar. The moral of the story? "Never bet the devil your head."
Besides the ironic humor, and the clear criticism of moral tales, "Never Bet the Devil Your Head" is also a satire on Transcendentalism. As Dammit approaches the bridge, his friend notes he is in an unusually happy mood and may, in fact, "be affected with the transcendentals," a disease.
After losing his head, the narrator notes "he did not long survive his terrible loss." After his death, the narrator sends a bill to the Transcendentalists but "the scoundrels refused to pay it." Instead, Toby Dammit's body was ground into dog's meat — perhaps a fitting fate for one who was afflicted with the disease of the transcendentals.
I think Poe here was responding to the Transcendental idea of communing directly with God or "the over-soul." If one can communicate with God, why can't he also communicate with the Devil? The result, of course, is disastrous (and hilarious). As a "moral tale," the story satirizes not only the Transcendentalists and their writings but also of popular writing in general. Poe, of course, called didacticism in literature a "heresy" which detracted from the inherent art of writing. But feel free to forget that stuff. Ultimately, "Never Bet the Devil Your Head" is simply a funny story — and very much worth reading. I've got one more post on my favorite of Poe's September stories coming soon.
For more on Poe's battles with Transcendentalism, mark your calendar for October 31. I'll be presenting a talk called "Poe vs. Transcendentalism" — in Concord, Massachusetts, of course.