"Never Bet the Devil Your Head" is a darkly comic short story by the American author Edgar Allan Poe. It first appeared in print, under the title of "Never Bet Your Head: A Moral Tale", in the September 1841 issue of the Philadelphia publication Graham's Magazine. It was published again, under the title by which it is now known, in the August 16, 1845 issue of the New York City newspaper the Broadway Journal.
The story concerns a young man named Toby Dammit who is very fond of saying, "I'll bet the Devil my head." Inevitably, the Devil eventually takes him up on that wager and things end badly for Dammit.
Readers should be aware that "Never Bet the Devil Your Head" contains quotations in Spanish and Arabic (which Poe translates) and quotations in Latin (which are left untranslated by Poe).
The story has been adapted for radio and film.
The story's narrator (obviously a fictionalized version of Edgar Allan Poe himself) states that he has been accused of writing stories that do not have morals. The narrator asserts that this is not true because critics are capable of finding a moral in any work of fiction, whether the author intended it to have that moral or not. Nevertheless, the narrator decides to respond to this criticism by writing a story which has its moral clearly set out in its title.
The tale concerns the unfortunate Toby Dammit. The narrator knows Toby Dammit from the time that he is a baby. Toby Dammit's mother tries to raise him well by beating him constantly. Unfortunately, she is left-handed. Since being beaten with the right hand makes children better behaved, it follows that being beaten with the left hand makes their behavior worse. Consequently, Toby Dammit grows up to be lustful, drunken and boastful. He also falls under the influence of the transcendentalists. Dammit is very fond of swearing, cursing and using phrases which sound like he is laying a bet. Nobody ever takes him up on those wagers, however. Also, since he is very poor, Toby Dammit never bets money. Instead, he uses expressions such as, "I'll bet you what you please", "I'll bet you what you dare", "I'll bet you a trifle" or "I'll bet the Devil my head". Eventually, he stops using the other expressions and only ever says, "I'll bet the Devil my head". The narrator finds this vulgar and pleads with Dammit to stop saying it. His pleas, however, fall on deaf ears.
One day, the narrator and Toby Dammit are out walking together. They enter a long covered bridge that crosses a river. The covered bridge has few windows and it is dark inside. There are several obstacles on the ground. Toby Dammit insists on jumping over them. At the bridge's exit, there is a high turnstile. The narrator goes through it. Toby Dammit says that he will jump over it in a flamboyant style. The narrator tells him not to boastfully claim that he can do something which is impossible for him. Dammit says that he will bet the Devil his head that he can jump over the turnstile.
The narrator suddenly becomes aware of the presence of a little old man wearing a black suit and a black silk apron. The old man says he is certain that Toby Dammit can jump over the turnstile in a flamboyant manner. He gets Toby Dammit to move back so that he can take a running leap at the turnstile. The old man says that he will say, "one, two, three and away" and that Dammit should start running when he says, "and away". The narrator wonders what business the old man has in getting Toby Dammit to jump. He says to himself that he will not jump if the old man asks him to do so, adding that he does not care who the devil the old man is. The narrator hears his last words come echoing back to him.
Toby Dammit comes running up to the turnstile and almost jumps over it. He falls down on the same side of the turnstile from which he started. The old man goes up to Toby Dammit. He takes something which he wraps up in his apron before he leaves. The narrator goes over to Toby Dammit and sees that he has lost his head. He sees that there is an iron bar over the exit to the bridge and decides that Toby Dammit must have struck his head against it.
In spite of having lost his head, Toby Dammit does not die straight away. He is treated by a homeopathist for several days. Nevertheless, Toby Dammit eventually dies. The narrator sends the bill for Dammit's funeral to the transcendentalists. When they refuse to pay, the narrator has Toby Dammit's body exhumed to be sold for dog food.
"Never Bet the Devil Your Head" is one of three short stories by Edgar Allan Poe that were adapted for the 1968 French-Italian film Histoires extraordinaires (released in the United States as Edgar Allan Poe's Spirits of the Dead and in the United Kingdom as Tales of Mystery). The segment loosely based on "Never Bet the Devil Your Head" was directed by Federico Fellini. In the English-language version of the movie, it is called "Toby Dammit". It is the only one of the three segments in the film in which the action takes place in the present-day. The segment stars Terence Stamp as Toby Dammit, a former Shakespearean actor who is struggling with alcoholism. Dammit comes to Rome to make a movie. He sees the Devil in the form of a little girl who is playing with a ball.
An American radio drama faithfully adapted from "Never Bet the Devil Your Head" was produced as an episode of The CBS Radio Workshop. The episode first aired in the United States on July 28, 1957. It stars John Dehner as Edgar Allan Poe (the narrator), Daws Butler as Toby Dammit and Howard McNear as the Devil.