Never Bet the Devil Your Head is an adaptation of Edgar Allen Poe’s 1841 satire, which Poe subtitled “A Moral Tale.” Toby Dammit is a young man of dubious morals. When he was a child, his left-handed mother beat him from left to right, and Poe says that if a proper right-handed beating dispels malice from a child, then it stands to reason that a left-handed beating knocks wickedness in. Toby enjoys drinking, smoking, telling lies in confessions to the priest, and gambling. Since he owns nothing of value, his favorite wager is, “I’ll bet the devil my head.” His best friend, the narrator, implores him to stop using this expression before it gets him into real trouble.