O. Henry Joins the Greats

The Library of America enshrines a satirical wit who portrayed desperate writers

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No discussion of the iconoclast in American literature can get very far without mention of William Sydney Porter, a.k.a. O. Henry, who was just 47 when cirrhosis of the liver cut short his troubled life on June 5, 1910.

The inclusion of O. Henry in the Library of America canonizes a vast body of work in which a certain type of story shines. Not surprisingly for such a prolific writer, some of O. Henry’s fictions succeed better than others. But those in the former category have all the wit and dark irony of Ambrose Bierce, and their surprise endings pack as much of a wallop as anything Guy de Maupassant or Agatha Christie put to paper, and O. Henry’s sensibility is distinctly that of a writer at modernism’s threshold. His style is neither too formal nor too loose. He likes to slather on the descriptive detail, yet never wastes a word.

O. Henry

The Library of America collection, 101 Stories, runs to 840 pages, the last 60 of which are given over to well-written, informative endnotes, textual notes, and a chronology of the author’s life. O. Henry wrote at a furious pace throughout much of his career and produced a body of tales that puts writers with much greater longevity to shame. Given the escapades that filled his life, it is no surprise that his fictional personae so often are people on the edge, namely struggling writers, alcoholics, drifters, runaways, jilted lovers, desperadoes, and outlaws. Sometimes his protagonists are lawmen with a thankless job to do.

Not seldom was O. Henry himself on the wrong side of the law. After his arrest on charges of having embezzled money from a bank in Austin, Texas, where he worked as a teller, in 1894, O. Henry made a sudden decision to forego a court appearance and flee to Honduras, which had no extradition treaty with the U.S. There he hid out while weighing his options. It would take someone with deep knowledge of pop culture to answer this question, but this critic can’t help wondering whether certain lyrics of another hard-living iconoclast, Warren Zevon, might be based on or inspired by the life of O. Henry: “And I’m hiding in Honduras, / I’m a desperate man. / Send lawyers, guns, and money, / The shit has hit the fan!”

The Western writer

If O. Henry were alive and writing today, he might be in trouble for reasons other than the alleged embezzlement. In a number of his tales, he depicts conflicts and customs of the Old West in a way that seems at odds with popular perceptions. We have all heard, and maybe at some point or other used, expressions like “It’s the Wild West over there!” in reference to a dicey and chaotic place.

Such slurs convey the attitude that the American West was a place of anarchy, where lawlessness and violence reigned and good and evil were in the eyes of whoever held the biggest gun. But the truth is far more complex. In point of fact, many people in the Old West had a highly developed sense of morality and ethics and lived by codes of conduct that have been all too sadly absent in the supposedly enlightened, progressive cities of the northeast.

O. Henry’s home in Austin, Texas. (Photo for Book and Film Globe by Ken Kurson)

While there are academic treatments of this subject, notably Roger D. McGrath’s superb Gunfighters, Highwaymen, and Vigilantes: Violence on the Frontier, explications of these themes can be harder to find in fiction. But O. Henry won’t give up the bone. In his story “A Technical Error,” a man who has suffered the loss of his dearest ones goes after the killer with rough justice in mind, but comes up against a serious hurdle when the lout mingles with a respectable lady. Under the code, you can’t gun down a criminal, even the most vicious kind, when he’s with a member of the fair sex. Later on, in the kind of ironic twist O. Henry does masterfully, the criminal’s effort to make use of a ruse to hide his identity gives the avenger just the chance he’s waiting for.

In another Western story, O. Henry’s iconoclasm again comes to the fore as he introduces the reader to Radcliff Conrad, the sheriff of Sikiwah County, Arizona, a man whose sensitivity is endearing even when it shades into acute self-doubt. Oddly for a sheriff, Conrad feels himself to be a physical coward and wants to run away from, not toward, the sound of gunfire. Maybe his biggest fear is that people will find out how far his real self is from the macho man he projects.

Here is a Western yarn with a sensitive, tormented hero, far ahead of its literary time. With his vivid, lean style and his channeling of the inner life of a complex lawman, O. Henry has written a Western story that bridges a gap between the modernism of which he was an early pioneer and the postmodernism whose exemplar is David Foster Wallace. That’s no mean feat for a Western story. In the end, when put to the test, Conrad’s actions rise to the level of heroism in keeping with the code that animates the better folk of the so-called Wild West.

In “Buried Treasure,” two rivals for the love of a beautiful woman named May Martha Mangum set off together to find a rumored stash of gold and silver. One of the treasure-hunters, Goodloe Banks, is highly educated and never ceases boasting about his vastly better schooling or teasing the narrator about the likely outcome of their courtship of May. Surely she will go for the learned man. The quest for the buried gold and silver leads to a different, most unexpected treasure, but not before Goodloe has given up tolerating his less literate companion and abandoned the search. “Buried Treasure” is a story reminiscent of the work of Wisconsin writer Hamlin Garland, who liked to remind readers of the folly of looking down on people because you have a Ph.D. and they are unschooled.

Henry’s western tales are inexhaustibly interesting. It is one of sociologist Howard Becker’s insights that those dubbed lawless or crazy do not live without rules so much as, at least in some cases, different ones. Some of them, anyway. In a story told from the point of view of an outlaw, “Holding Up a Train,” we see that a robber can be acutely aware of the amorality of men he works with and lament the fact that former fellow conspirators are all too willing to turn state’s evidence and help prosecute each other. It’s a story with broad implications. The treachery to which men willingly resort in this line of work calls for caution, our narrator explains. “That is why the man who holds up trains picks his company with a thousand times the care with which a careful girl chooses a sweetheart.”

The real lesson here? “And it is one of the reasons why the train-robbing profession is not so pleasant a one as either of its collateral branches—politics or cornering the market.”

Rare versatility

It shouldn’t take an iconoclast to drive home this simple truth, but geography is not a chain binding the writer by the ankle. The choice is not between trying to be Louis L’Amour writing about the West or Jay McInerney capturing the literary scene in New York. O. Henry turns his satirical lens on both. It is perhaps a bit of a shame that his Manhattan stories tend to eclipse those set in the provinces, but the New York tales are pretty good. The most famous may be the widely anthologized “The Furnished Room,” in which a lovelorn young man comes to a rooming house on the lower west side, believing that the girl who left him has stayed somewhere in the area if not in that very residence, and in his sadness and desperation succumbs to the fate that overtook her.

Henry’s subjects often are the less fortunate of this world, and it is in rendering the struggles of the literary, journalistic, and publishing scenes that his wit lends even the darkest narratives their sardonic hue. In “No Story,” a reporter is so desperate for a scoop that he falls for the most outlandish bait, peddled by an acquaintance who purports to know of a young woman who planned to marry a country lad but came to the city in search of the man she really loved, and who is now holed up in a rooming house without the money to pay for her lodgings or pay her way back home. Anyone who gives away the twist at the end of this story is a scoundrel, but the narrator’s amusement matches the reader’s.

In “The Plutonian Fire,” the narrator encourages a desperate writer manqué—an O. Henry trope—to wrack his imagination over and over, without concern for his long string of failures, until he comes up with a passable story. This acquaintance, Pettit, who came up from Alabama to New York with hopes of getting by as a fiction writer, requires a copious amount of whiskey to get past his writer’s block, but, as in many O. Henry stories, victory is Pyrrhic and short-lived. We all know a Pettit or have known one. Given the author’s tumultuous life, this story reads like autofiction in its least disguised form.

Another tale, “Elsie in New York,” is about a girl who arrives in the city with a heart as full of dreams as that of any number of young people. Her experiences as she bounces from one prospective employer to another drive home the reality of a place far more sordid than the West so widely deprecated by those who have never set foot there. Fortunately, there are civic-minded people looking out for poor innocent Elsie. New York has its good side. In a hilarious scene, a member of a temperance society warns her not to go to work for a confectioner, because the seemingly benign old man is putting rum in the candy. Elise has angels on her shoulders, but she does need to eat.

It is impossible to sum up all 101 stories here. You need to read them and let O. Henry’s voice and sensibility settle in your mind. You may come to feel a bit like Raggles, the wanderer and aspiring poet to whom O. Henry introduces readers in “The Making of a New Yorker.” The author details the distinct frustrations that Raggles has come to know with other cities. (“Chicago seemed to swoop down on him. . . . Raggles would awake to a sense of shivering cold.” “New Orleans had simply gazed down on him from a balcony.” “Boston construed herself to the poetic Raggles in an erratic and singular way. It seemed that he had drunk cold tea and that the city was a white, cold cloth that had been bound tightly around his brow.”)

Then Raggles makes his way to New York, where he comes face to face with indifference and rejection, with life’s pettiness and brutality, and all but loses hope until, in another parallel with Hamlin Garland, the aftermath of an accident on the street makes him see things in a different light.

Imagine going through a similar process to that of Raggles, but with authors rather than cities in mind. Weighing some of O. Henry’s contemporaries, you may find that Upton Sinclair was a muckraking reporter posing as a novelist and really didn’t write all that well, that Henry Adams was a pompous high-society toff who wrote for other pompous high-society toffs, that Zane Grey spun some good yarns but had limited range as a Western writer, that you agree with Charles Bukowski’s savage assessment of Theodore Dreiser’s bloated novels, that you’re not in the mood for Henry James, and that Mark Twain was great but you don’t feel like reliving high school just now by going back and rereading him, and ditto for Stephen Crane.

But when it comes to American literature of the time, you still have lots of options—101 of them right here.

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Michael Washburn

Michael Washburn is a Brooklyn-based writer and journalist and the author, most recently, of The Uprooted and Other Stories (2018), When We're Grownups (2019), and Stranger, Stranger (2020). He's also host of the weekly Sea of Reeds Media podcast, Reading the Globe.

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