John O’Hara, one of the great listeners of American fiction, understood how often people leave unsaid what is really on their minds. PHOTOGRAPH BY OSCAR WHITE / CORBIS / VCG VIA GETTY

John O’Hara never tired of complaining about how underestimated he was, and he had a point, even if he made it far too often. He was a gifted and sensitive writer, with talents quite different from those of his more highly regarded contemporaries: Hemingway, Faulkner, Fitzgerald. His strength and his limitation was that he was stubbornly earthbound. There are no similes in his work, no flights of lyricism or fancy writing, no hints of a deeper meaning beyond the moment. Nothing in O’Hara is “like” anything else. Things are vibrant and valuable for their own sake, and he described them—the make of a car, the cut of a suit, the song on the radio, the brand of cigarette, the sound of a broken tire chain on a snowy morning—with a scrupulousness that bordered on devotion.

Pottsville, Pennsylvania, when O’Hara was born, in 1905, was the prosperous commercial center of Pennsylvania’s anthracite region. His father was a successful and respected physician there, and the family belonged to the country-club, horse-riding gentry. Yet, because he was Irish and Catholic, O’Hara felt himself to be an outsider, and all his life, even after he had become wealthy and famous, he retained an outsider’s neediness and sullen defensiveness. His face was pressed against a glass that sometimes wasn’t there. But, the way outsiders do, he also became an uncanny observer of the world around him, someone who noticed everything. His father’s early death, in 1925—together with Dr. O’Hara’s history, it turned out, of living far beyond his means—ended O’Hara’s dream of going to Yale, which would have been for him, he fantasized, what Princeton was for Fitzgerald. Instead, he got a more practical and—for his kind of writer—more useful education knocking around, spending marathon hours in speakeasies and working at a series of small-town newspapers. He became, among other things, one of the great listeners of American fiction, able to write dialogue that sounded the way people really talk, and he also learned the eavesdropper’s secret—how often people leave unsaid what is really on their minds.

In the late twenties, O’Hara began publishing in The New Yorker, beginning an association that, with time out for feuds and hurt feelings, lasted some forty years, to the immense benefit of both parties. For O’Hara, the magazine became a place where he could develop his talent almost experimentally—without the pressures and expectations that went with novel writing—and he, in turn, became one of the magazine’s most frequent and valued contributors. His earliest efforts, like most of what the magazine was publishing then, were virtually plotless little sketches—often snatches of overheard dialogue: a lonely man in a diner, for example, reminiscing about an old girlfriend. (“So Nan and I just chatted about nothing at all. I didn’t make a pass at her and finally she suddenly stopped talking and I knew she was tired so I went home. Funny how you get over a girl like that.”) He also worked on three ongoing series: stories recounting the proceedings of the Orange County Afternoon Delphian Society, a New Jersey ladies’ club; stories about a company called Hagedorn & Brown, a New York manufacturer of paint and varnish; and stories that take the form of reports from the greens committee of a suburban country club. These stories are all satirical, making fun of Babbittry, small-town hypocrisy and narrow-mindedness, but the humor is mostly as fond as it is pointed, and the characters are never caricatures. Similarly, O’Hara’s slice-of-life sketches are never condescending, and, perhaps because he continued writing from outsiderdom, a habit of affection and generosity toward his people, even the meanest and most disagreeable, went on to become an O’Hara hallmark.

The first of his New Yorker stories that O’Hara thought worthy of book publication was “On His Hands,” a monologue in which a callow young man reveals more about himself than he intends to. It was republished in 1935 in O’Hara’s first collection, “The Doctor’s Son and Other Stories,” a volume that catches O’Hara in the process of becoming the writer we know. There, among the sketches, are a handful of stories as good as anything O’Hara ever wrote, including the long autobiographical title story, O’Hara’s earliest account of his fraught relationship with his formidable father—a love story, really, if a frustrated, unrequited one—and “Over the River and Into the Wood,” a formally daring story, remarkable (especially for a writer still in his twenties) in its ability to evoke the mind of a sixty-five-year-old who has just ruined his life. O’Hara’s talent didn’t evolve, exactly—for a while he went on writing sketches, doing finger exercises, so to speak—but suddenly it found its proper scope. There are traces of Hemingway here, a hint of Fitzgerald, but the voice is unmistakably his own, brisk with the confidence of a young man who already knows his way around in the world. The stories here, about people who drink and flirt too much, and suffer afternoon hangovers of regret, come from lived experience but also show a wry and sympathetic understanding.

All the pieces in O’Hara’s next collection, “Files on Parade,” published in 1939, are full-fledged stories, and yet they retain, as do most of the stories published over the next decade, a sketch-like lightness and brevity—they grab your attention before you know where they’re going. O’Hara later boasted that he wrote most of them in just a single sitting, and at The New Yorker he became famous for refusing to revise them afterward if the editors thought some clarification was needed. Yet a sense of speed and of economy is just what makes the best of these stories so thrilling. They seem to skim over the surface before allowing the reader to plunge into moments of unexpected death and feeling, like the heartbreaking revelation at the end of “Summer’s Day,” when an overheard conversation casts a bleak, autumnal shadow over what had seemed an ordinary day at the beach.

In 1949, O’Hara pretty much quit writing stories, and he didn’t resume for more than a decade. He had been quarrelling with The New Yorker, because he felt, among other things, that the stories he wrote for the magazine were so specialized that he couldn’t sell them elsewhere, and so he should be paid a kill fee for those that didn’t work out. The New Yorker’s very negative review of his novel “A Rage to Live” was the last straw. He poured his energy into writing novels, which, as he never tired of pointing out, had become far more profitable. O’Hara returned to the fold in 1960, allowing The New Yorker to publish his novella “Imagine Kissing Pete” (the title is one of O’Hara’s most provocative and inspired), and a flood of stories followed, close to a hundred in just the next three years. “I discovered I could begin again and do it better,” O’Hara wrote. “I had an apparently inexhaustible urge to express an unlimited supply of short story ideas. No writing has ever come more easily to me.”

Many of these new stories were longer and plottier than those that preceded them. Several of them are narrated by a successful writer named James Malloy, an O’Hara alter ego, and take the form of reminiscence. O’Hara had by then made a very happy third marriage, to Katharine Bryan, and, having for decades been a notoriously angry drinker, had given up alcohol entirely. He was easier in his own skin, and it shows a little in the writing: there are fewer stories about loneliness, isolation, or exclusion. Many of these later stories are set in the present—Lyndon B. Johnson is President, and people who used to go bars or speakeasies are staying home and watching television—but some of the best revisit the tone and setting of the Gibbsville stories of the thirties and forties: “How Old, How Young,” for example, a story of mismatched lovers, with an ending made thrillingly sensuous for not being spelled out, and “Christmas Poem,” a story of late-adolescent unhappiness and frustration that ends on a note of piercing sweetness, when a young man comes home on Christmas Eve, after discovering that a girl he’s in love with has been deceiving him, and finds his father, with whom he had quarrelled earlier, writing a poem to his mother: “He went to his room and took off his clothes, to the bathroom and brushed his teeth. He put out the light beside the bed and lay there. He wondered if Henrietta Cooper’s father had ever written a poem to her mother. But he knew the answer to that.”