O'Henry stories cover a wide range of subjects, but tend to classify into several genres. Most predominate are the love stories set in New York City: two people meeting in usual circumstances fall in love (or, sometimes, not) in unexpected ways. In one story two lovers are separated by distance, and unexpectedly re-united when the guy returns to NYC and sees part of a love-note to him accidently typed into the menu at the restaurant that contracts with the girl. Another story brings two lovers together because one gal at a boarding house was lacking two pennies for meat, so she had to meet other tenets, two of whom were looking for each other without knowing where the other had gone.
Often these love stories highlight the difference between the wealthy and the poor. In one, one department store girl is seeking after millionaires and dumps her boyfriend when she finds one interested in her. Her simple factory-worker friend takes a liking to the old boyfriend, and when they meet again, the millionaire’s new wife discovered that her friend had found love; all she had was money. In another, a department store girl hunting for millionaires turns one down because he talks about a honeymoon on the canals of Venice, the cafes of Paris, etc., and she thinks he is talking about the Coney Island amusement park (and therefore, she assumes he is not another wannabe millionaire).
There are criminal stories, which often feature Jeff Peters, who despite being a swindler nonetheless feels that his patrons should receive something of substance in return. Jeff Peters recounts one swindle where they sold stock in a ficticious corporation and when the plan goes awry and the original mastermind disappears, he returns as much money as he can (to the astonishment of the onlooking newspaper reporter) to the people, because they were relying on the investment. In another story of Peters', he meets with two other swindlers while on the run from a town where his business was no longer welcome. One is a lower-level card-swindler, while the other is a stock-swindler. Peters swindles the lower-level guy by simply marking the cards, but is then himself swindled by the stock guy when he invests the proceeds of the card swindling in a ficticious gold mine.
A number of stories are set in the American West, generally in the Texas area. In one, gal who married a millionaire for the money moves to her newly deceased husband’s ranch in Texas as his millions were a little overstated and this was all that was left. While there, she falls in love with the guy she turned down to marry the millionaire (and, who actually owns the ranch but never let on). A second story describes a Texas store owner coming to NYC for the yearly purchase of the store’s fashionable clothing. He takes a liking to the shop girl assigned to make him feel at home; she thinks he’s just another guy who isn’t serious, but much to her surprise, he actually proposes with a ring (unlike the others, who merely talk), and she finds herself unexpectedly going to be a wife in Texas.
O'Henry’s stories tend to focus on the main character’s values. Sometimes there is an unexpected event that forces a choice that reveals the character’s values. For instance, Jimmy Valentine, safe-cracker extraordinaire, falls in love and is on the way to give away his tools, when his fiance’s sister gets trapped in her father’s new safe and Jimmy Valentine reveals himself by using his tools to crack the safe. Other times, the unexpected events reveal the consequences of the choices the characters have already made, such as when the girl who married the millionaire discovers that her friend made a better choice with the poor guy she had been seeing.
Often O'Henry will contrast values between several characters. A doctor who robs banks encounters a crook who treats his wife poorly; the doctor looks down on him because the doctor honors women, yet the crook would never betray a trust. Frequently this contrast occurs between rich and poor, highlighting the gulf between them. A man meets a woman at the park; the woman is a millionaire who is looking for a simple man, the man is simple and interested in her. She is somewhat aloof, and it turns out that she is a cashier at a restaurant pretending to be a rich woman and he is the owner of the luxury car she pretends is hers. Or the girl who thinks the descriptions of a honeymoon in Europe are Coney Island.
One of the best parts of O'Henry is the snapshot of life in the early 1900's. He must have been on the wrong side of the law at some point, because the mindset of the characters is perfect. Likewise, he must have lived in Texas, and perhaps South America, because the descriptions are vivid in an experiential way. His descriptions get to the essence, the character of whatever it is, without belabouring the point. If it is nature, you can picture the scene. If it is a person, you can imagine how they are feeling. Since many are set in NYC, after reading the collection, you can get a sense of what NYC was in 1900, how people lived, what they did for fun, their struggles, and even what it looked like. And to top it off, he often incorporates into his character descriptions references to literature, religion, and well-known cultural icons of the time (the latter being sometimes lost on this reader)
O'Henry stories are one of the best examples of the craft of short story-telling. The descriptions are concise, perceptive, insightful, and vivid. He deals with life that is dirty, yet has literary references to satisfy the higher minded. The twists are revealing of character, and satisfying in their fitness for the situation. His characters are multi-dimensional and give a sense that O'Henry truly understand people. If you like vivid imagery, real characters living in a real past, or enjoy suprisingly fitting endings, read O'Henry. After 100 years, his stories are still delightful.