I recently completed a heavy, hardcover edition of the Complete Works of O.Henry, clocking in at over 1300 pages. I was aware of some of O. Henry's writings, but had never actually sat down to read them for myself. The tome is comprised almost entirely of short stories, but also includes a few poems, letters and editorials.
Some of his writings are dated and the humour in particular has lost some potency, but his stories were, generally, written skillfully and cleverly. He seemed to love poking fun at his work as he was composing it, such as this aside in "A Night in New Arabia:"
"Don't lose heart because the story seems to be degenerating into a sort of moral essay for intellectual readers.
There will be dialogue and stage business pretty soon."
O. Henry is best remembered for "the Gift of the Magi," which is a well-polished story and representative of most of his work. Indeed, the "twist ending" of Magi is how his name is recalled today, the so-called "O. Henry ending." In fact, his work has endured criticism both contemporary and since that he was formulaic.
What can I tell you about the best of O. Henry's work? Well, let's start with his urban tales. O. Henry loved the city and set many of his romantic tales in locales like Manhattan, often bridging two people of different classes together through unlikely circumstances, but almost as often keeping the would-be lovers apart, such as in "While the Auto Waits." Some other great tales of the city include "the Cop and the Anthem," concerning a man desperate to spend a night in jail; "Mammon and the Archer" which poses the old question of whether money can buy love; "After Twenty Years" reunites two old friends who have wound up on separate sides of the law; a similar tale with a romantic bend is "Hearts and Hands;" in "the Fool-Killer" a man's love of liquor leads him to draw some paranoid conclusions; "Vanity and Some Sables" is a fine story of pride; and in "the Last Leaf" a woman concentrates on the last leaf on the branch by her window as she faces what might be her deathbed.
O. Henry loved the west. His more "rural" works include "the Caballero's Way," which introduced the Cisco Kid. Film, radio and television turned the Cisco Kid into a typical two-fisted hero of the old west, but O. Henry's original story is quite different. He's really a terrible man who finds a clever loophole to punish his unfaithful lover while maintaining the code of the Caballero. Some other great stories are "the Pimienta Pancakes" with two men pursuing the same woman, one with the aim of learning a pancake recipie; "Cupid a la Carte" where a woman working in a diner can't stand how men eat, driving her would-be suitors to literally starve themselves to win her favour; "the Princess and the Puma" where a woman saves a man's from a puma and he tries to turn the tables on her; "a Double-Dyed Deceiver" where a man on the run agrees to impersonate a wealthy heir; "Friends in San Rosario" where a bank examiner finds a singular discrepancy and has to be convinced of the trust of friendship; "the Hiding of Black Bill" concerns a drifter who takes up work on a farm soon after a certain robbery; "the Friendly Call" concerning two men whose quiet loyalty knows no bounds; "the Whirligig of Life" about a couple seeking divorce but find it a little too costly; "Red Roses of Tonia" has two men compete to deliver a hat to the woman they love; and "One Dollar's Worth" where a district attorney faces bloody vengeance.
Perhaps O. Henry's best tale of the west was "the Roads We Take," which has an unexpected twist that reframes the entire story.
O. Henry wrote a number of tales concerning a pair of grafters, told from the duo's point of view as they swindled various people out of their money. Often they get away with their schemes, sometimes they're outsmarted by someone a shade cleverer than they. The best of these stories include "Jeff Peters as a Personal Magnet" with a medicinal scam; "Modern Rural Sports" with a farming scam; "the Chair of Philanthromathematics" with a university scam; "the Exact Science of Matrimony" with a matrimonial service scam; "Shearing the Wolf" with a counterfeit money scam; and "Conscience in Art" with a fine art scam. All of these tales - collected together as the Gentle Grafter - are some of Henry's funniest material.
O. Henry wrote some splendid detective parodies; one of his Sherlock Holmes parodies, "the Sleuths" is a good example of his dated humour. It has many funny moments, especially for Holmes fans such as the passage:
"I remember a case that I brought to a successful outcome a year ago. A family bearing the name of Clark disappeared suddenly from a small flat in which they were living. I watched the flat building for two months for a clue. One day it struck me that a certain milkman and a grocer's boy always walked backward when they carried their wares upstairs. Following out by induction the idea that this observation gave me, I at once located the missing family. They had moved into the flat across the hall and changed their name to Kralc."
But "the Sleuths" is ruined by a dated punchline. Much better are the Holmes parodies "the Adventures of Shamrock Jolnes" and "the Detective Detector." He also sent-up the famous real-life detective Eugene Vidocq with his tales "Tictoq" and "Tracked to Doom," which are both quite funny.
Some other examples of O. Henry satirizing the fiction of his day are the medieval farce "the Prisoner of Zembla" and the burglar parodies "Makes the Whole World Kin" and "Tommy's Burglar" and stage play mockeries "a Strange Story" and "Fickle Fortune or How Gladys Hustled." His story "Confessions of a Humorist" may not be autobiographical, but it is very funny.
And then there are some O. Henry stories which are quite different from everything else. "Holding up a Train" is supposedly told from the view of an authentic outlaw; it certain feels authentic. "Roads of Destiny" follows three possible outcomes for its protagonist, but all come down to the force of destiny; his "Bexar Scrip No. 2692" is a pretty good crime story.
Overall, I highly recommend O. Henry to people who enjoy early 20th century short fiction, especially if you like the whimsy found in writers like Damon Runyon, John Collier or M.R. James. I don't think you need to bother with his complete works as I did, but if you find the best collections - say, the Four Million, Heart of the West and the Gentle Grafter - you'll do just fine.