10 of the Best O. Henry Short Stories Everyone Should Read

By Dr Oliver Tearle (Loughborough University)

The stories of the US short-story writer O. Henry, real name William Sydney Porter (1862-1910), are characterised 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 ten 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 …

1. ‘The Gift of the Magi’.

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 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 …

2. ‘Mammon and the Archer’.

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 gift 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.

3. ‘Memoirs of a Yellow Dog’.

In this 1903 story, the yellow dog of the story’s title recounts his life, his owners, and his love for his master (and his dislike for his master’s wife). Man and dog really do have a stronger bond in this story than man and wife.

The story is narrated by a yellow dog who lives in New York. He cannot remember any details of his birth but can remember an old lady trying to sell him to a ‘fat lady’ on Broadway. This woman made a fuss of the dog and talked to him in a rather cutesy way, calling him ‘um oodlum, doodlum, woodlum, toodlum, bitsy-witsy skoodlums’ (which means … well, it’s anybody’s guess, really). She calls him Lovey.

The dog is openly contemptuous of the things the lady does during the daytime, while her husband is out at work, and hatches a plan to turn things around for himself – and the husband …

4. ‘The Duplicity of Hargraves’.

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.

5. ‘The Last Leaf’.

This 1907 story is among his most famous: along with ‘The Gift of the Magi’ it may be the best-known O. Henry story of all.

It focuses on two female artists and their male friend, also an artist. One of the two women falls ill with pneumonia and it looks likely she will die of the disease – she herself believes that she will perish when the last leaf of the year falls from the last tree. We won’t spoil the ending, but we will say that the male friend, Mr Behrman, plays an important role in the story’s twist ending.

6. ‘The Sleuths’.

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 realises 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?

7. ‘After Twenty Years’.

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.

8. ‘The Skylight Room’.

A young typist rents a room in a boarding-house: the topmost room in the house, hence the title of this 1906 tale. Although the coincidences in this story may strain credulity, part of the fun of an O. Henry story is trying to work out what the twist will be before it comes, and here the author uses names and naming as an integral part of this tale, as the young typist, Miss Leeson, becomes more and more poverty-stricken until she literally faints from hunger. But a star will come to her rescue …

9. ‘Conscience in Art’.

This 1907 story is about two con men who go to visit an art collector, and hatch a plan to sell the wealthy man a rare carving. But is the carving – supposedly one of only two of its kind in existence – all that it appears to be? As this is an O. Henry story, we know there’s a twist coming …

10. ‘The Ransom of Red Chief’.

We’ll conclude this pick of classic O. Henry short stories with a 1907 story with a comic twist at the end. Two men kidnap the son of a wealthy man from Alabama, hoping to demand a large ransom for the boy’s safe return. Unfortunately for them, their hostage will prove to be extremely testing company …