By the early 1920s, F. Scott Fitzgerald had a prose ready to say almost anything. His trouble was that he didn’t have anything ready to say with it. There’s artistry in his fourth book, the collection of short stories published in 1922 as Tales of the Jazz Age, but it’s the artistry of an artist adrift. At sea. At a loss for how to steer himself from the fog bank into which he’d sailed.

Part of that fog was financial. The eleven short stories in Tales of the Jazz Age had all previously appeared in magazines, for the money that would make Fitzgerald the highest-paid periodical writer of his time. And, man, did he need the money. Living a life of extravagance, a profligate man with an even more profligate wife, he would find himself forced to write his way out of debt again and again, and magazine prose was always the easiest path. He said of one of the stories in the book that he wrote it in a single day, “with the express purpose of buying a platinum and diamond wrist watch which cost six hundred dollars.”

Fitzgerald’s problem was that he was “whoring” himself, Ernest Hemingway complained, taking genuine artistic ideas and ruining them by replotting them into something more popular—while glittering the stories up with tinsel prose to become what magazine editors wanted for their readers: pictures of young love with a tinge of shivery doom or a rightwising boy-regains-girl ending, all flavored with a teaspoon of sex appeal.

Just as Fitzgerald’s first short story collection, Flappers and Philosophers, was timed to complement his first novel, This Side of Paradise, in 1920, so Tales of the Jazz Age was released to coincide with his second novel, The Beautiful and Damned, in 1922. Aware of the stories’ gossamer quality, and wanting to be taken more seriously as a writer, Fitzgerald thought his important work the previous year had been writing the chapters of The Beautiful and Damned, appearing serially in Metropolitan magazine, and the revising of them for the novel’s publication. But he had also written some magazine stories—for the likes of the Saturday Evening Post, Smart Set, Collier’s, Vanity Fair—in the two years since Flappers and Philosophers. And why let them languish? So he pitched his editor at Scribner’s, Max Perkins, on the idea, and Perkins, noting the enduring sales of story collections from Rudyard Kipling and Richard Harding Davis, agreed.

The problem was the stories’ lack of unity. What is a reader supposed to make of a story as evanescent as “The Camel’s Back,” a drunken comedy about two men in an animal costume, in the same volume as the historical farrago of “Tarquin of Cheapside,” a tale of a sexual assault supposedly committed by Shakespeare in the sixteenth century? And both of them alongside “The Lees of Happiness,” about the fading of a once-well-known author portentously named “Curtain”?

Fitzgerald did make an attempt to unify the stories with a strange and deliberately overwritten descriptive table of contents. Two of what Fitzgerald’s contents page called “Fantasies” are the most remembered stories in Tales of the Jazz Age: “The Curious Case of Benjamin Button,” about a figure who regresses from birth as an old man to death as an infant, and “The Diamond as Big as the Ritz,” which describes a murderous, slave-holding family in Montana made incredibly wealthy and wildly insane by their diamond mine. But the most revealing story, the tale of the Jazz Age that helps us define Fitzgerald’s quandary in the early part of the 1920s, is one he placed in the first part of the book, in the section he titled “My Last Flappers.”

That story is “May Day.” Fitzgerald was lost, intellectually and artistically—like the rioting ex-soldiers in “May Day,” who “don’t know what they want, or what they hate, or what they like”—even while he was pouring out prose he knew was good: “Just finished the best story I’ve done yet,” he wrote Perkins about “The Lees of Happiness,” and The Beautiful and Damned “is going to be my life masterpiece.” There’s a wry self-awareness in that hyperbole, of course, as there is when, in the table of contents, he gives the title of “Unclassified Masterpieces” to the final third of the stories in Tales of the Jazz Age. But he always knew that prose wasn’t his artistic failing. What he needed was a point. A purpose. A reason for his art. What he needed was a topic as big as his talent.

This Side of Paradise had made Fitzgerald a national star for “the countless flappers and college kids who think I am a sort of oracle,” he told Perkins. But he understood that the Jazz Age, whose name he had popularized, was coming to an end. The first section of Tales of the Jazz Age was labeled “My Last Flappers” for a reason. In 1931 Fitzgerald would write in an essay called “Echoes of the Jazz Age” that the word jazz “in its progress toward respectability, has meant first sex, then dancing, then music. It is associated with a state of nervous stimulation, not unlike that of big cities behind the lines of a war. To many English the War still goes on because all the forces that menace them are still active—Wherefore eat, drink and be merry, for tomorrow we die. But different causes had now brought about a corresponding state in America—though there were entire classes (people over fifty, for example) who spent a whole decade denying its existence even when its puckish face peered into the family circle.”

“It was an age of miracles, it was an age of art, it was an age of excess, and it was an age of satire,” he would look back on the Jazz Age to declare. By 1923, however, it was essentially finished for the young, as the once-censorious older generations took it over and hedonized themselves, discovering “that young liquor will take the place of young blood, and with a whoop the orgy began.”

But if the Jazz Age of Fitzgerald’s youth was coming to an end, if he had written the last of his flappers, what was left? Even as he solved the structural problems that reviewers had noticed in This Side of Paradise (reaching toward the perfected novelistic form he would produce with The Great Gatsby in 1925), he had to find somewhere to go beyond The Beautiful and Damned, with its tale of a flapper wife, Gloria Gilbert, and her artist husband, Anthony Patch, who partied their way through the Jazz Age until they “wrecked on the shoals of dissipation.”

So, in “May Day,” America itself begins rising up—really, for the first time in Fitzgerald’s work—toward the central theme it would become in The Great Gatsby. Oh, there had been hints here and there. Intimations. Nods toward the dialogue Fitzgerald would place in the 1931 story “Babylon Revisited”: Asked if he lost much in the crash of 1929, the character Charlie replies, “‘I did,’ and he added grimly, ‘but I lost everything I wanted in the boom.’”

“May Day” has Fitzgerald’s artistry turning openly toward not just young Americans but the nation as a historical entity, a dense thing that needs understanding. The story takes place during the May Day riots of 1919, when socialists in New York and other cities rallied to protest the recent conviction of Eugene V. Debs and America’s anti-communist interventions in Russia. A wealthy group of Yale alumni have come to New York for a dance at the same time that demobilized World War I veterans are filling the streets, drinking their way from bar to bar.

The key figure in the story is Gordon Sterrett, both a Yalie and a war veteran. Meeting his college friend, Philip Dean, Sterrett explains that he needs to borrow three hundred dollars to pay off a woman named Jewel Hudson, who is blackmailing him—which leads Dean to mock him as “bankrupt—morally as well as financially” and agree only to give Sterrett eighty dollars.

Fitzgerald then turns to follow two angry and drunken demobbed soldiers, Carroll Key and Gus Rose, who end up sneaking into the dance, mingling with the wealthy young people—among whom is Edith Bradin, Sterrett’s former college girlfriend. She has plans to escape her date, Peter Himmel, and reconnect with Sterrett, as she imagines him through the gauze of memory. But when she sees what dissolution and the war have done to him, she recoils. Leaving the dance, she goes to see her brother, Henry Bradin, a radical who works at a socialist newspaper and, she believes, disapproves of her.

Outside on the streets, the veterans have begun breaking up the socialist marches and breaking random heads, turning New York into an unfocused riot. They end up attacking the newspaper office, where Henry Bradin’s leg is broken and Key dies when thrown out a window. Meanwhile, Himmel, knowing that he has lost Edith, begins drinking with the lower-class ex-soldier Rose. Jewel Hudson crashes the dance, looking for her blackmailed lover, Sterrett. The whole drunken crew eventually ends up at a restaurant, getting thrown out after starting a food fight and shouting at the waiters.

The next morning, in a cheap Sixth Avenue hotel, Sterrett wakes to learn that in a drunken stupor the night before he had married Jewel. He leaves, buys a gun, and returns to his own rundown apartment, where he shoots himself, sprawling across the “drawing materials” that hearkened back to the talent he had let himself ruin.

What are we to do with a story like this? Passages of descriptive prose are broken by sudden intrusions of an ironic narrator:

The great plate-glass front had turned to a deep creamy blue, the color of a Maxfield Parrish moonlight—a blue that seemed to press close upon the pane as if to crowd its way into the restaurant. Dawn had come up in Columbus Circle, magical, breathless dawn, silhouetting the great statue of the immortal Christopher, and mingling in a curious and uncanny manner with the fading yellow electric light inside.

followed by:

Mr. In and Mr. Out are not listed by the census-taker. You will search for them in vain through the social register or the births, marriages, and deaths, or the grocer’s credit list. Oblivion has swallowed them and the testimony that they ever existed at all is vague and shadowy, and inadmissible in a court of law. Yet I have it upon the best authority that for a brief space Mr. In and Mr. Out lived, breathed, answered to their names and radiated vivid personalities of their own.

The socialists, the ex-soldiers, the rich, the poor, the young, the old: no one in the story comes off well, and Fitzgerald offers no real account of the nation beyond the sheer material vileness of the American scene in 1919. As if to row back into the fog, he even follows “May Day” in the “My Last Flappers” section of Tales of the Jazz Age with “Porcelain and Pink,” a brief pseudo-play about a nineteen-year-old girl in a bathtub, talking vivaciously through the window with a boy who can’t quite see down to her nineteen-year-old nudity. Comedy, in other words: a P.G. Wodehouse story stripped to the frisson of scandal, and the most notorious of Fitzgerald’s magazine stories.

Still, something had changed with “May Day,” something new set afoot. The “Fantasies” that he published in 1922—“The Diamond as Big as the Ritz” and “The Curious Case of Benjamin Button,” the most recent magazine work Fitzgerald had done at the time of the book’s publication—are rightly remembered as the best stories in Tales of the Jazz Age, but their fantastical elements were a dead end for him. It is possible to read “The Diamond as Big as the Ritz” as an allegory for America, with the story’s wealth-obsession, lingering race slavery, and violence, all set in a Wild West that is somehow a combination of both a frontier past and a science-fiction future. But a more direct line, a serious effort to raise his art to grasp the Condition of the Nation, connects “May Day” to The Great Gatsby.

“The poor son-of-a-bitch,” the only mourner at Gatsby’s wake declares—a line Dorothy Parker repeated at Fitzgerald’s own funeral in 1940. There’s a sadness a reader may feel when reading Tales of the Jazz Age, a feeling of the artist adrift. At sea. At a loss. More than any other genuinely great writer with a genuinely great novel, F. Scott Fitzgerald seems incomplete: a talent as big as the Ritz, a prose as good as any American has ever had, not quite producing all that he could have. All that he should have.