Never Bet the Devil Your Head

'Never Bet the Devil Your Head: A Moral Tale', later republished as 'Never Bet the Devil Your Head', 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, at least in part due to his left-handed mother flogging him with her left hand, which is considered improper. Dammit often made rhetorical bets, becoming fond of the expression 'I'll bet the devil my head'. Although the narrator tries to break Dammit of bad habits, he fails. Nevertheless, the two remain friends.