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Never Bet the Devil Your Head
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 little old man. The old man is interested in seeing if Dammit is capable of making such a leap and offers him a good running start. The narrator thinks to himself that it is improper for an old man to push Dammit into making the attempt—"I don't care who the devil he is," he adds.
The narrator watches as Dammit makes a perfect jump, though directly above the turnstile he falls backwards. The old man quickly grabs something and limps away. The narrator, upon checking on his friend, sees that Dammit's head is gone ("what might be termed a serious injury"). He realizes that just above the turnstile, lying horizontally, was a sharp iron bar that happened to be lying at just the spot where his friend's neck hit when he jumped. The narrator sends for the "homeopathists", who "did not give him little enough physic, and what little they did give him he hesitated to take. So in the end he grew worse, and at length died". After the bill for his funeral expenses is left unpaid, the narrator has Dammit's body dug up and sold for dog meat.
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 little old man. The old man is interested in seeing if Dammit is capable of making such a leap and offers him a good running start. The narrator thinks to himself that it is improper for an old man to push Dammit into making the attempt—"I don't care who the devil he is," he adds.
The narrator watches as Dammit makes a perfect jump, though directly above the turnstile he falls backwards. The old man quickly grabs something and limps away. The narrator, upon checking on his friend, sees that Dammit's head is gone ("what might be termed a serious injury"). He realizes that just above the turnstile, lying horizontally, was a sharp iron bar that happened to be lying at just the spot where his friend's neck hit when he jumped. The narrator sends for the "homeopathists", who "did not give him little enough physic, and what little they did give him he hesitated to take. So in the end he grew worse, and at length died". After the bill for his funeral expenses is left unpaid, the narrator has Dammit's body dug up and sold for dog meat.
16 pages, ebook
First published January 1, 1841
About the author
Edgar Allan Poe
10.6k books29.6k followersThe name Poe brings to mind images of murderers and madmen, premature burials, and mysterious women who return from the dead. His works have been in print since 1827 and include such literary classics as The Tell-Tale Heart, The Raven, and The Fall of the House of Usher. This versatile writer’s oeuvre includes short stories, poetry, a novel, a textbook, a book of scientific theory, and hundreds of essays and book reviews. He is widely acknowledged as the inventor of the modern detective story and an innovator in the science fiction genre, but he made his living as America’s first great literary critic and theoretician. Poe’s reputation today rests primarily on his tales of terror as well as on his haunting lyric poetry.
Just as the bizarre characters in Poe’s stories have captured the public imagination so too has Poe himself. He is seen as a morbid, mysterious figure lurking in the shadows of moonlit cemeteries or crumbling castles. This is the Poe of legend. But much of what we know about Poe is wrong, the product of a biography written by one of his enemies in an attempt to defame the author’s name.
The real Poe was born to traveling actors in Boston on January 19, 1809. Edgar was the second of three children. His other brother William Henry Leonard Poe would also become a poet before his early death, and Poe’s sister Rosalie Poe would grow up to teach penmanship at a Richmond girls’ school. Within three years of Poe’s birth both of his parents had died, and he was taken in by the wealthy tobacco merchant John Allan and his wife Frances Valentine Allan in Richmond, Virginia while Poe’s siblings went to live with other families. Mr. Allan would rear Poe to be a businessman and a Virginia gentleman, but Poe had dreams of being a writer in emulation of his childhood hero the British poet Lord Byron. Early poetic verses found written in a young Poe’s handwriting on the backs of Allan’s ledger sheets reveal how little interest Poe had in the tobacco business.
For more information, please see http://en.wikipedia.org/wiki/Edgar_al...
Just as the bizarre characters in Poe’s stories have captured the public imagination so too has Poe himself. He is seen as a morbid, mysterious figure lurking in the shadows of moonlit cemeteries or crumbling castles. This is the Poe of legend. But much of what we know about Poe is wrong, the product of a biography written by one of his enemies in an attempt to defame the author’s name.
The real Poe was born to traveling actors in Boston on January 19, 1809. Edgar was the second of three children. His other brother William Henry Leonard Poe would also become a poet before his early death, and Poe’s sister Rosalie Poe would grow up to teach penmanship at a Richmond girls’ school. Within three years of Poe’s birth both of his parents had died, and he was taken in by the wealthy tobacco merchant John Allan and his wife Frances Valentine Allan in Richmond, Virginia while Poe’s siblings went to live with other families. Mr. Allan would rear Poe to be a businessman and a Virginia gentleman, but Poe had dreams of being a writer in emulation of his childhood hero the British poet Lord Byron. Early poetic verses found written in a young Poe’s handwriting on the backs of Allan’s ledger sheets reveal how little interest Poe had in the tobacco business.
For more information, please see http://en.wikipedia.org/wiki/Edgar_al...
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Displaying 1 - 30 of 134 reviews
September 13, 2023
Cuento de corte surrealista. Poe lo define como cuento con moraleja.
Está narrado en primera persona y trata sobre la relación entre dos amigos, uno es el narrador y el otro es Toby Dammit. Toby, aun siendo pobre, tiene tendencia a apostar su cabeza ante cualquier reto. Nuestro narrador acaba harto de esta circunstancia hasta que llega una prueba y aparece, de repente, un personaje siniestro.
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A surrealistic tale. Poe defines it as a moral tale.
It is narrated in the first person and is about the relationship between two friends, one is the narrator and the other is Toby Dammit. Toby, though poor, has a tendency to bet his head on any challenge. Our narrator becomes fed up with this until a trial occurs and a sinister character suddenly appears.
Está narrado en primera persona y trata sobre la relación entre dos amigos, uno es el narrador y el otro es Toby Dammit. Toby, aun siendo pobre, tiene tendencia a apostar su cabeza ante cualquier reto. Nuestro narrador acaba harto de esta circunstancia hasta que llega una prueba y aparece, de repente, un personaje siniestro.
----------------------------------
A surrealistic tale. Poe defines it as a moral tale.
It is narrated in the first person and is about the relationship between two friends, one is the narrator and the other is Toby Dammit. Toby, though poor, has a tendency to bet his head on any challenge. Our narrator becomes fed up with this until a trial occurs and a sinister character suddenly appears.
September 25, 2026
Never Bet the Devil Your Head – A Tale with a Moral another deliciously wicked ten-pager by Edgar Allan Poe, was a real treat. A nice break from the deeply expansive Bleak House I am currently reading.
Toby Dammit (…a Dickensian type name, note), is the protagonist here. In short, he’s a bit of a cocky, mouthy type. He’s often big-mouthing his way around town and challenging others that he would “Bet the Devil my Head” – regarding anything even remotely contestable. His bravado is as vacuous as is his intellect.
The devil makes an appearance and it’s easy to guess what the outcome is here. The narrator (expressing Poe’s satirical views – I reckon) is funny, and is clearly making fun of Dammit here. Repeated stupidity, resulting in an inevitable outcome.
The ending is gruesome, and then some. A perfectly dark piece of writing by this brilliant author.
One bit I particularly liked was his piss-take of pseudoscientists namely, Phrenologists* and Homeopathists**. Further reading revealed Poe really didn’t like these branches of ‘science and medicine,’ something that makes me like Poe even more!!
.
4 Stars
* A field of ‘science’ whereby a person’s personality and traits can be interpreted by the shape of their skull.
** A field of ‘science’ whereby people can be cured by a very diluted potion of the substance that is causing them an issue in the first place.
Toby Dammit (…a Dickensian type name, note), is the protagonist here. In short, he’s a bit of a cocky, mouthy type. He’s often big-mouthing his way around town and challenging others that he would “Bet the Devil my Head” – regarding anything even remotely contestable. His bravado is as vacuous as is his intellect.
The devil makes an appearance and it’s easy to guess what the outcome is here. The narrator (expressing Poe’s satirical views – I reckon) is funny, and is clearly making fun of Dammit here. Repeated stupidity, resulting in an inevitable outcome.
The ending is gruesome, and then some. A perfectly dark piece of writing by this brilliant author.
One bit I particularly liked was his piss-take of pseudoscientists namely, Phrenologists* and Homeopathists**. Further reading revealed Poe really didn’t like these branches of ‘science and medicine,’ something that makes me like Poe even more!!
.
4 Stars
* A field of ‘science’ whereby a person’s personality and traits can be interpreted by the shape of their skull.
** A field of ‘science’ whereby people can be cured by a very diluted potion of the substance that is causing them an issue in the first place.
October 25, 2022
Fairly clever little story, but I just couldn’t really get into it for some reason.
October 15, 2015
Moraleja: hay apuestas que se pierden desde el inicio y con más facilidad si el diablo mete la cola en ellas.
November 6, 2021
The whole time I was reading this the Mario Bava film played in my head.
October 15, 2017
A boy named Toby Dammit would always bet his head to the devil for everything and one day it came true. It is a short story by Edgar Allan Poe written in response to the criticism that he faced regarding his work.
November 20, 2018
Every time I read this story I laugh. Poe is so sarcastic. It comes across as a big "F you" to his critics and a dig at those branches of thought he found silly. I'm laughing now just thinking about it.
January 24, 2013
This short story is part of The Complete Works of Edgar Allen Poe.
My Synopsis: Mr. Toby Dammit has always been a troubled young man--due to his mother being left-handed and that rather then beating the evil out of him, she inadvertently beat it in--fond of drink and women and especially gambling. Unfortunately, one should never bet the devil his head...
My Thoughts: Oh my, this is one of the funniest things I've read in ages! I was rolling right from the start... Poe is best known, of course, for chilling Gothics and moody, beautiful poetry, but a lot of people don't realize he was also a brilliant satirist and wit, and this short piece shows exactly why he was so considered. Wonderfully, wickedly, hilariously funny!
My Synopsis: Mr. Toby Dammit has always been a troubled young man--due to his mother being left-handed and that rather then beating the evil out of him, she inadvertently beat it in--fond of drink and women and especially gambling. Unfortunately, one should never bet the devil his head...
My Thoughts: Oh my, this is one of the funniest things I've read in ages! I was rolling right from the start... Poe is best known, of course, for chilling Gothics and moody, beautiful poetry, but a lot of people don't realize he was also a brilliant satirist and wit, and this short piece shows exactly why he was so considered. Wonderfully, wickedly, hilariously funny!
September 4, 2025
Note finale : 3.5/5
Lu dans le recueil "La Chute de la Maison Usher et autres histoires extraordinaires" des éditions RBA coleccionables.
Dix-septième nouvelle du recueil. Et encore une fois, une nouvelle amusante. Je ne savais pas qu'Edgar Poe écrivait autant de comédie noire. En l'occurrence, un jeune homme très désagréable passe son temps à parier sa tête au diable et au bout d'un moment, le diable vient récupérer son dû. Donc on est sur de l'horreur mais très clairement aussi sur de la comédie et qui fonctionne assez bien.
Lu dans le recueil "La Chute de la Maison Usher et autres histoires extraordinaires" des éditions RBA coleccionables.
Dix-septième nouvelle du recueil. Et encore une fois, une nouvelle amusante. Je ne savais pas qu'Edgar Poe écrivait autant de comédie noire. En l'occurrence, un jeune homme très désagréable passe son temps à parier sa tête au diable et au bout d'un moment, le diable vient récupérer son dû. Donc on est sur de l'horreur mais très clairement aussi sur de la comédie et qui fonctionne assez bien.
April 22, 2020
2 stars, because I respect that Poe disapproved of transcendentalism and that he believed all fiction should have a moral; but no more stars than that because the presentation of the moral of this story was pretty boorish.
November 26, 2024
nie sądziłam że Poe mógłby napisać że dzieci i mięso są lepsze gdy się je tłucze XD
November 28, 2018
Never Bet the Devil Your Head is another quick and enjoyable Poe read, another you can complete in a single sitting when you want to pass a small amount of time.
Although this is not my favourite Poe read, it was an interesting little tale. You knew where things were going, yet that did not prevent you from enjoying the outcome. With the sarcasm I’ve come to expect of Poe, Never Bet the Devil Your Head is a pleasing little read.
Although this is not my favourite Poe read, it was an interesting little tale. You knew where things were going, yet that did not prevent you from enjoying the outcome. With the sarcasm I’ve come to expect of Poe, Never Bet the Devil Your Head is a pleasing little read.
October 25, 2018
the moral of the story is....don't bet the devil your head.
July 23, 2022
just Poe being petty, such an icon
November 29, 2020
3.5 Stars
rounded up to 4 Stars.
I love Poe's wit in the way he responded to the "ignoramus" [Poe's word] critics that said his tales had no moral to impart to readers.
Never Bet the Devil Your Head is often subtitled A Tale with a Moral. "This satire was Poe's literary response to the charge by critics writing in the Transcendentalist magazine The Dial that his fiction lacked moral content. He takes the inclusion of a moral in the story to a ridiculous extreme [O Boy did he! When one ticked Poe off he went after you like a Pit Bull] by making every incident he relates a cause for the expression of yet another principle. Despite assertions of his contempories that Poe's satire is aimed at literary pedanticism, transcendentalism, and The Dial, Poe denied having any specific targets. Instead he wrote, 'The tale in question is a mere Extravaganza leveled at no one in particular, but hitting right and left at things in general.' " Sova Dawn B. (2001). Edgar Allan Poe, A to Z : the essential reference to his life and work. New York: Checkmark Books. (170) "Poe once wrote in a letter to Thomas Holley Chivers that he did not dislike transcendentalists, 'only the pretenders and sophists among them.' " Silverman, Kenneth. (1991). Edgar A. Poe: Mournful and Never-ending Remembrance. New York: Harper Perennial. (169)
NOTE:
"Transcendentalism was a movement [by the German philosopher Immanuel Kant] of philosophical idealism that rejected the emphasis on empirical inquiry of the 18th-century Enlightenment and focused instead on the value of the senses and intuition in revealing truth. . . . Poe rejected the idea of the idealism of the movement, which rather than turn to scientific measurement and inquiry to make sense of the world, believed that pure reason in the absence of external evidence would elicit an immediate perception of truth. Unlike the transcendentalists, most of the narrators and characters in Poe's stories and poems cannot trust their senses are eliciting truths or correctly representing their situations, nor can we as readers. Further, in his preoccupation with scientific advances, Poe appeared to have rejected the idealism that pervaded the thinking of the Transcendentalists." Sova Dawn B. (2001). Edgar Allan Poe, A to Z : the essential reference to his life and work. New York: Checkmark Books. (241)
I love Poe's wit in the way he responded to the "ignoramus" [Poe's word] critics that said his tales had no moral to impart to readers.
Never Bet the Devil Your Head is often subtitled A Tale with a Moral. "This satire was Poe's literary response to the charge by critics writing in the Transcendentalist magazine The Dial that his fiction lacked moral content. He takes the inclusion of a moral in the story to a ridiculous extreme [O Boy did he! When one ticked Poe off he went after you like a Pit Bull] by making every incident he relates a cause for the expression of yet another principle. Despite assertions of his contempories that Poe's satire is aimed at literary pedanticism, transcendentalism, and The Dial, Poe denied having any specific targets. Instead he wrote, 'The tale in question is a mere Extravaganza leveled at no one in particular, but hitting right and left at things in general.' " Sova Dawn B. (2001). Edgar Allan Poe, A to Z : the essential reference to his life and work. New York: Checkmark Books. (170) "Poe once wrote in a letter to Thomas Holley Chivers that he did not dislike transcendentalists, 'only the pretenders and sophists among them.' " Silverman, Kenneth. (1991). Edgar A. Poe: Mournful and Never-ending Remembrance. New York: Harper Perennial. (169)
NOTE:
"Transcendentalism was a movement [by the German philosopher Immanuel Kant] of philosophical idealism that rejected the emphasis on empirical inquiry of the 18th-century Enlightenment and focused instead on the value of the senses and intuition in revealing truth. . . . Poe rejected the idea of the idealism of the movement, which rather than turn to scientific measurement and inquiry to make sense of the world, believed that pure reason in the absence of external evidence would elicit an immediate perception of truth. Unlike the transcendentalists, most of the narrators and characters in Poe's stories and poems cannot trust their senses are eliciting truths or correctly representing their situations, nor can we as readers. Further, in his preoccupation with scientific advances, Poe appeared to have rejected the idealism that pervaded the thinking of the Transcendentalists." Sova Dawn B. (2001). Edgar Allan Poe, A to Z : the essential reference to his life and work. New York: Checkmark Books. (241)
August 25, 2024
i giggled
January 6, 2018
Από τον ποε περίμενα κάτι καλύτερο, όπως πολλή καλά ξέρουμε ότι ο ποε έχει κάνει κάποια πολύ καλά βιβλία και γενικά η γραφή του είναι πολύ ιδιεταιρη και μερικές φορές πολύπλοκη. Αυτό το βιβλίο είναι αρκετά έξυπνο με μαύρο χιούμορ αλλά σε κουράζει, βεβαία είναι ένα καλό βιβλίο για να αρχίσεις να διαβάζεις ποε αλλά είναι πολλά μυθιστορήματα που δεν βγάζουν κανένα νόημα είναι ένα μέτριο μικρό βιβλίο που ναι μεν έχει κάποιες καλές στιγμές αλλά εγώ προσωπικά δεν τρελάθηκα περίμενα κάτι διαφορετικό!
March 30, 2021
Un pequeño cuento oscuro con la moraleja puesta en el título. No hay duda: Edgar Alan Poe, usted es diabólico Jajajaja 😂
Este breve relato trata del trágico destino de su joven amigo Toby Dammit. Donde Poe utiliza el apellido de este amigo, como una pequeña premonición a su fatal y cruel destino: “Damm it”, que en inglés significa ”maldita sea”. ☹️🎻 Pero ¡momento! que aquí no se trata de un destino basado en la mala suerte, ya que a pesar de lo breve de la historia si llegamos a conocer qué Dammit pasó por violencia familiar. Lo que según Poe afianzó su forma de ser y lo llevó a vivir un trágico destino. ¿Debatible, no? 🤔
De todas formas, les dejo el dato: este pequeño cuento también se encuentra gratis en Apple Books. 📚 Algo chiqui como para despedir marzo. ✌️🤓
Este breve relato trata del trágico destino de su joven amigo Toby Dammit. Donde Poe utiliza el apellido de este amigo, como una pequeña premonición a su fatal y cruel destino: “Damm it”, que en inglés significa ”maldita sea”. ☹️🎻 Pero ¡momento! que aquí no se trata de un destino basado en la mala suerte, ya que a pesar de lo breve de la historia si llegamos a conocer qué Dammit pasó por violencia familiar. Lo que según Poe afianzó su forma de ser y lo llevó a vivir un trágico destino. ¿Debatible, no? 🤔
De todas formas, les dejo el dato: este pequeño cuento también se encuentra gratis en Apple Books. 📚 Algo chiqui como para despedir marzo. ✌️🤓
April 6, 2026
Edgar dostawał dużo krytyki, że każda opowieść "powinna" kończyć się morałem, których u niego raczej nie widać. No to napisał coś z morałem. Nie odgadniecie, Toby Dammit który miał się nigdy nie zakładać z diabłem o głowę, założył się z diabłem o głowę... i stracił głowę!
also myślałam że walnę jak padło stwierdzenie "dzieci, podobnie jak twarde kotlety lub nowoczesne, greckie oliwki, są bez porównania lepsze, gdy są bite" xD
także końcówka mnie zabiła. Narrator poprosił o pieniądze na pogrzeb przyjaciela Tobiego, ale ich nie dostał, więc odkopał ciało i sprzedał je na psią karmę xDDDDD tego się nie spodziewałam
also myślałam że walnę jak padło stwierdzenie "dzieci, podobnie jak twarde kotlety lub nowoczesne, greckie oliwki, są bez porównania lepsze, gdy są bite" xD
także końcówka mnie zabiła. Narrator poprosił o pieniądze na pogrzeb przyjaciela Tobiego, ale ich nie dostał, więc odkopał ciało i sprzedał je na psią karmę xDDDDD tego się nie spodziewałam
October 3, 2025
Meh.
It was ok, but not worth reviewing.
For the moment at least.
It’s public domain. You can find it HERE.
-----------------------------------------------
PERSONAL NOTE :
[1841] [24p] [Horror] [Not Recommendable]
-----------------------------------------------
Meh.
Estuvo ok, pero no vale la pena reseñarlo.
Al menos por ahora.
Es dominio público, lo pueden encontrar ACA.
-----------------------------------------------
NOTA PERSONAL :
[1841] [24p] [Horror] [No Recomendable]
-----------------------------------------------
It was ok, but not worth reviewing.
For the moment at least.
It’s public domain. You can find it HERE.
-----------------------------------------------
PERSONAL NOTE :
[1841] [24p] [Horror] [Not Recommendable]
-----------------------------------------------
Meh.
Estuvo ok, pero no vale la pena reseñarlo.
Al menos por ahora.
Es dominio público, lo pueden encontrar ACA.
-----------------------------------------------
NOTA PERSONAL :
[1841] [24p] [Horror] [No Recomendable]
-----------------------------------------------
September 18, 2017
Sometimes I forget how great a satirist Poe was, and this story just proves it.
"I bedewed his grave with my tears, worked a bar sinister on his family escutcheon, and for the general expenses of his funeral sent in my very moderate bill to the transcendentalists. The scoundrels refused to pay, so I had Mr. Dammit dug up at once, and sold him for dog’s meat. "
"I bedewed his grave with my tears, worked a bar sinister on his family escutcheon, and for the general expenses of his funeral sent in my very moderate bill to the transcendentalists. The scoundrels refused to pay, so I had Mr. Dammit dug up at once, and sold him for dog’s meat. "
December 29, 2021
Agradezco mucho que es un relato corto.
Es mi primer acercamiento a Edgar Allan Poe y no estuvo tan mal, pero me desesperó en ciertos párrafos.
Es mi primer acercamiento a Edgar Allan Poe y no estuvo tan mal, pero me desesperó en ciertos párrafos.
May 16, 2022
Mildly amusing. Plenty ridiculous.
October 13, 2022
Leave it to Poe to come up with a gruesome morality tale.
January 29, 2023
He never disappoints
April 19, 2023
*Read in an Edgar Allan Poe Tales of Horror Collection*
I'm so here for sassy Poe 😆
A moral story wrapped up in a neat little package; 1800's language and phrasing sure is something else 🙈
I'm so here for sassy Poe 😆
A moral story wrapped up in a neat little package; 1800's language and phrasing sure is something else 🙈
September 15, 2021
It wasn’t bad and parts were funny, but overall it just felt okay. I think I prefer Poe’s horror and mystery 😉
November 4, 2023
funny, well-written story. the diction really reminds me how far the English language has come a hundred years since.
i also thought it a bit surrealistic.
i also thought it a bit surrealistic.
February 1, 2024
3.5⭐️
que final…
que final…
October 28, 2023
This story was one of my favourites when I was thirteen. I remain somewhat impressed that I understood it (twenty years ago) at such a young age.
Also, it's so funny, offbeat, and strange!
Also, it's so funny, offbeat, and strange!
Displaying 1 - 30 of 134 reviews






























