Is Poe's “Never Bet the Devil Your Head” a mere trifle, or is it a tale warranting serious attention? More than just a satirical farce, this overtly comic story from 1841 is a rhetorical lampoon of what Daniel Royot dubs “the Transcendentalist postulation of secret essence.” Deriving archetypal elements of plot and characterization from two earlier Poe tales, “The Bargain Lost” and “Bon-Bon,” “Never Bet the Devil Your Head” combines “the fantastic” with what Poe labels “the quaint in phraseology.” In other words, Poe unleashes a tale of uncertain identity, rhetorical flourish, and double meaning, where the hapless victim of an ill-fated pigeon-wing over a turnstile may or may not be a boy's pet dog. If he is a dog, the protagonist is no ordinary dog, but an oath-making product of the narrator's fancy, acting in comic juxtaposition with the narrator's erudite schemes of language—and his penchant for whingeing. If he is not a dog, however, then he is no less ill-fated owing to a lack of what J. A. Cuddon calls the Transcendentalist emphasis on “individual conscience.” Still, the real lesson of “Never Bet the Devil Your Head” is not the titular moral, but the satirical substitution of rhetorical minutiae for “secret essence.”

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