1 . 5 of the Best O. Henry Short Stories Everyone Should Read

The stories of the US short-story writer O. Henry, real name William Sydney Porter (1862-1910), are characterized by their irony and by their surprise endings, which became something of a signature of a good O. Henry short story. However, another word that is often used to describe O. Henry’s short stories is ‘sentimental’, and it is for this reason, perhaps, that he is no longer appreciated as he perhaps should be, despite the wit of O. Henry’s narrative style and the cleverness of his twist endings.

Below, we select and introduce five of O. Henry’s very best short stories. Many of them are only five pages long in the average paperback reprint of his stories (we recommend in particular 100 Selected Stories (Wordsworth Classics), which is excellent value for money), so can be ready in no more than ten minutes. What are you waiting for?

Most (though not all) of these stories are included in the anthology mentioned above. O. Henry was a prolific writer so even those 100 collected in that fat volume aren’t his full, collected works...

This is surely O. Henry’s best-known story of all. Published in 1906, it’s about a husband and wife, Jim and Della, buying Christmas presents for each other, without much money to spend on them. The two of them have a special possession they prize above all others: Jim has a gold watch that’s been MAGI handed down through the generations, and Della has her long, thick hair.

How will Della be able to raise the money to buy Jim a gold chain for his watch? We won’t say any more...

This story is also from 1906. A retired soap manufacturer named Anthony Rockwall worships ‘Mammon’, i.e., money above everything else. The ‘Archer’ of the story’s title is Cupid, the god of love.

Rockwall tells his son Richard that money can buy him anything in life, but Richard points out that the girl he loves is leaving in a few days' time and he hasn’t managed to win her hand. He takes a ring with him, which his mother left to him in her will, with the intention of asking his sweetheart to marry him but he drops the ring and... well, we won’t say more, but let’s just say that once again, O. Henry’s gif for twist endings turns things around...

The story is a curious counterpoint to ‘The Gift of the Magi’, in which a married couple uses their last few dollars to buy each other a Christmas present. Here, there is a suggestion that money can buy you time, after all.

First published in 1902, this story is about the elderly Major Pendleton Talbot and his spinster daughter Lydia. After the pair move to Washington D. C. from the American South, they meet Henry Hopkins Hargraves, a vaudeville actor.

However, the impecunious Major and his daughter are shocked, when they go to see a show, to find Hargraves impersonating the Major in front of the audience. Then a man claiming to be one of the Major’s former slaves from the antebellum era turns up and offers to help the pair out of hardship...

As ever, we won’t spoil the ending. But let's just say the word ‘duplicity’ in this story’s title itself has a double meaning.

This 1911 story is a more light-hearted tale from O. Henry, and a pastiche of the popular Sherlock Holmes stories.

A man searching for his missing sister in New York realizes the official police detective can’t help him. Only one man can: the famous private consulting detective Shamrock Jolnes. As the narrator informs us: ‘The famous sleuth’s thin, intellectual face, piercing eyes, and rate per word are too well known to need description.’ Sound familiar?

This 1906 story is a tale of a reunion. Two men who grew up together in New York City agree to meet up, twenty years later, in the restaurant where they last bid each other farewell two decades ago in order to seek their fortunes. However, one of the men, Bob, has become a hardened criminal and the other man, Jimmy, has become — well, let’s not give too much away, other than to say the reunion does not exactly go according to plan.