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"Never Bet the Devil Your Head," often subtitled "A Tale With a Moral," is a short story by...

"Never Bet the Devil Your Head," often subtitled "A Tale With a Moral," is a short story by American author Edgar Allan Poe, first published in 1841. The satirical tale pokes fun at the notion that all literature should have a moral and spoofs Transcendentalism. The narrator, presented as the author himself, is dismayed by literary critics saying that he has never written a moral tale. The narrator then begins telling the story of his friend Toby Dammit. Dammit is described as a man of many vices, presumably at least in part due to his left-handed mother flogging him with her left hand, considered improper. Dammit often made rhetorical bets, becoming fond of the expression "I'll bet the devil my head." Though the narrator tries to break Dammit of bad habits, he fails. Nevertheless, the two remain friends. While traveling one day, they come across a covered bridge. It is gloomy and dark, lacking windows. Dammit, however, is unaffected by its gloom and is in an unusually good mood. As they cross the bridge, they are stopped by a turnstile partway across. Dammit bets the devil his head that he can leap over it. Before the narrator can reply, a cough alerts them to the presence of a