One hundred years after its publication in 1925, The Great Gatsby is the most popular of American novels and one of the most esteemed. Of its two principal rivals for preeminence, Moby-Dick lacks the common touch and The Adventures of Huckleberry Finn is no longer so respected. Gatsby’s lasting popularity is extraordinary for a serious novel. It has been translated into 42 languages, over 30 million copies have been sold worldwide, and hundreds of thousands of copies still sell annually in the United States. Admittedly, a large segment of the readership is a captive audience: almost every American high school student has to read it. That certainly sounds like success, especially for a highbrow modern artist.

But the masterpiece that ought to have made F. Scott Fitzgerald (1896–1940) comfortably rich, critically adored, confident in his talents, and happy, instead disappointed, disheartened, and all but eviscerated him. The big money and colossal adulation for the best book he ever wrote would arrive only well after his death, of a third heart attack, at age 44. The last royalty check he got for the novel was for $13.13. Failure could not have been more definitive. Rejection on all the counts that mattered most was all Fitzgerald could see. He could not appreciate the excellence of his own handiwork as long as the book-buying public failed to ratify it, and the praise lavished on The Great Gatsby by some of the literati provided scant consolation. Gertrude Stein honored it for “creating the contemporary world” after the manner of William Makepeace Thackeray’s Vanity Fair; Edith Wharton saw “how great a leap” it dared and she forecast “still greater things” from its author; and T.S. Eliot acclaimed it “the first step that American fiction has taken since Henry James.” But theirs were not the loud commanding voices in the marketplace that sold books. The most significant such voice was H.L. Mencken’s, who in his review called Gatsby “a glorified anecdote, and not too probable at that.”

And Fitzgerald was bent on writing books that sold in a big way. Early success had greeted him with an uproar at age 23 with the publication of his first novel, This Side of Paradise (1920), a Bildungsroman that ends with the young hero contemplating the Princeton generation that would follow his own and finding it “dedicated more than the last to the fear of poverty and the worship of success; grown up to find all Gods dead, all wars fought, all faiths in man shaken.”

Glitter and Dazzle

In 1918, two years before that first novel, Fitzgerald had fallen in love with Zelda Sayre, the daughter of a well-to-do judge. This formidable patriarch would presently become a justice of the Alabama Supreme Court, and he had little use for an upstart from nowhere with starry-eyed literary aspirations—an infantry officer who had never reached Europe and who had attended Princeton but failed to take a degree. But Zelda loved him more than she did most other men chasing her and she wanted to believe in him, so young Scott set to work winning the princess in the tower. She didn’t convince any more easily than her father, however, and she broke their engagement in 1919, scared off by his dim prospects: while working at a New York advertising agency by day and writing short stories and poems by night, he suffered through 122 rejection slips before landing a story with Mencken’s magazine The Smart Set, for which he got $30. That would not do. He quit his job, decamped to his parents’ house in St. Paul, Minnesota, and worked in a racehorse lather on This Side of Paradise. Max Perkins of Scribner’s, who would become the most celebrated editor in American literary history, bought the book, after the original version had been thoroughly revised; and one fine morning Fitzgerald woke up to find himself famous. His literary triumph at last assured him the hand of Zelda Sayre of Montgomery, an enchanting hellion with many determined suitors (pilots eager for a date would perform daredevil stunts above her house), and beating out the competition was no small part of his victory.

Energy bred success and success bred energy: his second novel, The Beautiful and Damned (1922), and two collections of short stories, Flappers and Philosophers (1920) and Tales of the Jazz Age (1922), followed in swift succession. Newspapers and publicity agents took to naming him the voice of his generation—a dubious distinction given the cavalier nihilism, unrelenting pleasure-seeking, and disillusion with everything, including disillusionment itself, endemic in that time and place. But then these were Fitzgerald’s subjects, the life he knew firsthand, which he embraced at first, came to despise, but could never completely renounce. For a wondrous spell no one embodied that glitter and dazzle more than he did. Being joyously lit and riding down Fifth Avenue on the roof of a taxicab or diving in evening dress with fabulous Zelda into some of New York’s most famous fountains made him immediately a legend: a hero for the Jazz Age flappers and philosophers to emulate.

He always understood, though, that quick, bright things come to confusion. During a cab ride one day (conventionally seated), he burst into tears at the realization that he was supremely happy and that this perfection could never be surpassed. The title of his third book of short stories, published right after The Great Gatsby, suggested the game was ending with serious debts demanding collection: All the Sad Young Men (1926). By this point stories sold to The Saturday Evening Post occasionally earned him as much as $4,000 a pop—over $80,000 in today’s money. He knew, however, that most of the stuff he was turning out for the slicks was second-rate at best, and that even at his feverish rate of production he and Zelda were consuming far more than he made. The only enduring pleasure that selling out his talent could buy—the cushioned security of gathered wealth—his spendthrift habits denied him.

His best efforts at literary excellence, meanwhile, most notably with Gatsby, won him meager reward, and the pickings got slimmer and slimmer as intellectual fashion changed. The literature of class struggle became popular in the years of the Great Depression, with paeans to solidarity with the suffering masses: the Joad family fleeing Dust Bowl Oklahoma for California’s promise and finding only oppression and despair in John Steinbeck’s The Grapes of Wrath (1939), Robert Jordan sacrificing himself for the Spanish Republic in Ernest Hemingway’s For Whom the Bell Tolls (1940), the inescapable penury of tenant farmers in rural Alabama who are so beaten down they cannot conceive of a better life in James Agee’s non-fiction epic Let Us Now Praise Famous Men (1941). The Jazz Age was over and tales of gilded youth disporting themselves or struggling through callow love affairs had seen their day.

Decay from Within

Fitzgerald was daunted by the changing atmosphere and by the terrible misfortune that would strike his own love for Zelda, and it took him nine years to produce his next novel, Tender Is the Night (1934), the last one he would finish. An impressive performance, and more of a popular success than he might have expected, it is the portrait of a brilliant young psychiatrist, Dick Diver, who marries a desolated patient of his, Nicole, beautiful and rich and traumatized by having been raped by her father. Expatriates on the Riviera and in Paris, they are the perfect café society couple for several years, until they both fall out of love, their marriage ends, and the doctor takes to anesthetizing himself with alcohol and winds up a small-town general practitioner in upstate New York.

Writing the novel cost Fitzgerald nearly everything. Nicole Diver’s fateful mental illness recapitulated Zelda’s own freefall into schizophrenia in 1930, and Dick Diver’s alcoholic wretchedness mirrored Fitzgerald’s own, down to the drunken street brawling that got both men special attention from foreign police. Zelda’s intermittent confinement in the best sanitariums had Fitzgerald sweating to pay the bills. The Saturday Evening Post, where he commanded top dollar for a time yet, became an invaluable resource; and when he wasn’t cranking out stories for them, he performed the menial labor Hollywood had to offer, as a screenwriter—a position denigrated by all in the industry’s creative elite but paying extremely well.

Zelda fought hard for her sanity and hoped to prove herself as an artist. Before falling ill, she had ferociously but quixotically tried to make herself into a trained ballet dancer. While hospitalized she took up painting, and Fitzgerald convinced a Manhattan gallery to exhibit her work. She wrote a novel based on her madness and her adulterous love affair (or was it only a flirtation?) with a French aviator, Save Me the Waltz (1932), which despite his serious reservations Fitzgerald helped get published, and which sank into the quicksand of critical dismissal and public indifference. In Some Unfinished Chaos: The Lives of F. Scott Fitzgerald (2023), Arthur Krystal quotes at some length from a 1933 transcribed interview the Fitzgeralds had with Zelda’s psychiatrist, during which the breadwinner asserted his exclusive artistic claim to the mother lode of their lives: “Everything we have done is mine…. I am the professional novelist and I am supporting you. That is all my material. None of it is your material.” Zelda for her part blamed her husband’s alcoholism and neuroticism for her plight, insisting that she preferred the “insane asylum” to life under his thumb. When she dismissed any happiness they had had as illusory and said their marriage had just been “a long battle,” Scott protested, “We were about the most envied couple in about 1921 America.” Zelda sneered in reply that they had been “good showmen.” Thus, storybook young love turned to hate with teeth bared and claws out.

Nevertheless, Fitzgerald did his best for the remainder of his life to ensure Zelda got the medical care she needed. It became harder and harder to earn the income required, and by 1937 the stories he was writing had become too dark for the sumptuous meal-ticket Saturday Evening Post, and he had to settle for simple bread and butter at $250 from Esquire. Screenwriting became his day job, which he never really mastered. The time for domination was long gone and survival was the order of the day. His decay from within and his efforts to recover are memorialized in his very powerful, posthumously published collection of essays, The Crack-Up (1945).

Obsessive Pursuits

The Great Gatsby is dedicated “Once Again to Zelda.” It might have been otherwise. For the first four years of their marriage, Fitzgerald was the proud possessor of the king’s daughter—the hero who had vanquished all comers to win her—and he just knew he would be Zelda’s lifelong boon companion in an extravaganza of effervescent wit, high spirits, gleeful intoxication, innocent sportiveness, and erotic thrills, and they would serve as models for their generation and be the envy of the known world. But Zelda’s romantic infidelity—she said it was just an emotional affair, though Fitzgerald, who could never be sure what had happened, declared the damage done irreparable—was a betrayal of ideal love that bled into his fictional creation. The most perfect love Fitzgerald could imagine—Jay Gatsby’s longing for Daisy Buchanan, whom the poor nobody had courted when she was the teenaged Daisy Fay of Louisville and to whom he believed he had won the right of everlasting possession—was doomed by its inevitable contact with imperfection. Not so much because it was adulterous and therefore morally objectionable, but because it was soiled by the grimy business through which Gatsby eventually acquired his vast wealth, and because Daisy was in the end too small, too common, for Gatsby’s vision of her, and perhaps most of all because the past cannot simply be erased, or for that matter relived, by an act of sovereign will.

Fitzgerald had a penchant for discerning the inescapable sadness in ordinary life—which is why he favored those persons of extraordinary vitality, the boldest and the tirelessly exciting, the ones who know life is meant for emotional exorbitance, for seizing the crown jewel of ecstasy even if you find it belongs to another man loath to part with it. There was nothing worse to Fitzgerald’s mind than the moral shame of the unlived life, which principally meant a dreary existence without the supreme pleasure of love at its exhilarating best.

The failure of the boldest, most vital, and most worthy of men to realize the happiness he seeks—more precisely, to hold firmly the happiness he reaches—is The Great Gatsby’s tragic innovation. The novel presents the most remarkable tale in modern literature of the obsessive pursuit of happiness in love, by a poor young man who transforms himself into the spectacular and near-legendary figure he imagines his beloved cannot possibly resist, who is willing to let nothing stand in the way of his attaining the prize, and whose perfected scheme to win her proves a flimsy idyll that cannot withstand the combined powers of accident and time and moral weakness, known more familiarly as inexorable black-hearted Fate.

Nick Carraway tells the story. He is a Yale graduate, a Great War veteran, and an apprentice Wall Street bond salesman, who lives in a cottage on the shore of Long Island Sound right next door to Gatsby’s mansion in the New York suburb of West Egg, a louche enclave of show people and other of the more disreputable moneyed types. Nick is no longer a young man—he turns 30 in the course of the novel. He comes from the Midwest, and returns there after the Gatsby fiasco, which has tainted the East in his eyes permanently: “I felt that I wanted the world to be in uniform and at a sort of moral attention forever; I wanted no more riotous excursions with privileged glimpses into the human heart.” At the same time, paradoxically, Nick says Gatsby alone “represented everything for which I have an unaffected scorn.” The reader will be expected to measure shrewdly the fascination that Gatsby’s daring, perseverance, “heightened sensitivity to the promises of life,” and unique sort of “romantic readiness” work upon this neighbor of (mostly) regular habits, inspiring in Nick a pride in Gatsby’s irreproachable honesty, and a disdain for new money unscrupulously come by and garishly spent.

Nick is swept up into Gatsby’s intrigue as a second cousin of Daisy Buchanan’s and a college acquaintance of her husband, Tom, a football hero, “a national figure in a way,” whose subsequent life could never equal in intensity his gridiron glory days. In the opening chapter Nick pays a call upon the couple, grandly established in the old money haven East Egg, right across an inlet of the Sound from West Egg. Tom’s wealth astonishes Nick: he has brought a string of polo ponies east from the exclusive North Shore suburbs of Chicago, and for a wedding gift gave Daisy a pearl necklace worth $350,000 (about $6.5 million today). What do you do with yourself, Fitzgerald implicitly asks, when you have everything most people will envy you for but you remain dissatisfied? This insufferable galoot exercises his scanty mind on white supremacist screeds and pampers his “cruel body” with serial adulteries of small consequence, most recently with Myrtle Wilson, the wife of a forlorn car mechanic and gas station owner. The Wilsons are denizens of the “valley of ashes” inhabited by the ill-fated poor, “the ash-gray men” whose lives the well-to-do commuters passing hurriedly through this wasteland every day find scarcely worth a glance and definitely not worth living. Why Tom married Daisy is not readily apparent.

Daisy for her part, it will become clear, married him because she needed material comfort and prestige, both of the highest order, and she says she has lived to regret it: “Well, I’ve had a very bad time, Nick, and I’m pretty cynical about everything.” Nick, however, detects “the basic insincerity” of her professed scorn for the ever so “sophisticated” life she has with Tom. “I waited, and sure enough, in a moment she looked at me with an absolute smirk on her lovely face, as if she had asserted her membership in a rather distinguished secret society to which she and Tom belonged.” Daisy and Tom are appallingly more of a piece than she is willing to admit to Nick or to herself. And this special understanding she shares with Tom will inevitably finish off her love for Gatsby.

A Remorseless Pagan Fate

Gatsby starts as a figure of mystery whose precious and perilous secrets are disclosed gradually over the course of the novel. When Nick first sees him, on a starry night of deep summer, standing alone on his lawn, Gatsby is examining the sky with the self-assured possessiveness of a very rich man, as though he had “come out to determine what share was his of the local heavens.” Then Gatsby stretches out his trembling arms as if beseeching and turns his gaze seaward, where the only thing visible is “a single green light, minute and far away, that might have been the end of a dock.” It is the light on the Buchanans’ dock, for Gatsby has bought his magnificent house because it is directly across the water from Daisy’s home. That light has of course become the most celebrated symbol of romantic yearning in American literature.

Gatsby’s parties have also acquired a mythic glamour, though it was really their gaudy vulgarity that Fitzgerald emphasized. At these preposterously ornate shindigs, gangs of the most “interesting people,” as Gatsby advertised them, many of them ever drunker on bootleg liquor and champagne as midnight sped toward dawn, carried on as at “an amusement park,” in Nick’s assessment. The parties were designed to make their host celebrated in the hope that Daisy would hear of them and want to attend. They fail in that intention, however, and Gatsby has to resort to asking Nick to invite Daisy for tea so that the lover might meet his beloved once again.

That meeting reignites Daisy’s passion for Gatsby; his own passion, it transpires, never wavered during the five years since he parted from Daisy Fay of Louisville, an officer on his way to war, promising he would come back for her. But the poor boy born James Gatz in North Dakota could only hope without hope to marry a rich girl like Daisy. That Daisy was rich fascinated Gatsby; “he had never been in such a beautiful house before,” and her material circumstances held the promise of unprecedented refinement and luxurious ease for him, inspiring a transcendent exaltation as though these were ineffable spiritual pleasures. He was captivated by the “ripe mystery” of “romances…fresh and breathing and redolent of this year’s shining motor cars and of dances whose flowers were scarcely withered.” “But he knew that he was in Daisy’s house by a colossal accident”; he did not belong in her world. Thus, his sexual possession of the young girl had an unsettling brutality: having misled Daisy into believing he too came from money and patrician family, he “took her because he had no real right to touch her hand.”

Only a fortune of his own would give him that right. The sort of romance he desired has a fixed cost, a dollar figure, and pity the suitor who cannot afford the purchase price—and double the pity for the young beauty who is purchased. A year after Gatsby left her, on the eve of her marriage to Tom, Daisy got “drunk as a monkey,” deposited the pearl necklace in a wastebasket, instructed a bridesmaid to go downstairs and announce the wedding was off, and burst into a protracted deluge of weeping, all the while clutching a letter from her true love overseas that slowly crumpled and dissolved when she was placed in the bath to sober up. The next day the wedding came off without a hitch. In short order, as the Buchanans roamed the world’s garden spots, it became clear to her what a faithless boor her husband was. When Gatsby comes back into her life in his alluring new incarnation, she is smitten with him even more than before.

Nick Carraway understands that even in Louisville Gatsby’s boundless imagination was brought up short by Daisy’s living presence. “He knew when he kissed this girl, and forever wed his unutterable vision to her perishable breath, his mind would never romp again like the mind of God.” His singular excellence is his devotion to the love he has chosen from the unlimited possibilities for his life that he had imagined with incalculable intensity. Daisy cannot fathom how extraordinary Gatsby’s romping mind was or how inviolable his love for her has always been and will always be. When she finally attends one of Gatsby’s parties, she experiences a tremor of fear that there is nothing uniquely remarkable about her—that “some authentically radiant young girl” might come out of the crowd and in “one moment of magical encounter” claim Gatsby for her own. She does not realize this is impossible. Gatsby’s love is not subject to such accidents; it is an impregnable destiny, without fear and without reproach, and in its perfection atones for the “colossal accident” that brought him into her life in the first place.

For Daisy, however, there are imperfections on her lover’s part that are cause for unspoken reproach; Gatsby feels it and it stings. She finds West Egg uncouth, meretricious, and appalling, and doesn’t enjoy herself at Gatsby’s party. As Tom jeers, “Did you notice Daisy’s face when that girl asked her to put her under a cold shower?” Later, as the story’s momentum gathers, Tom, who has dug into Gatsby’s past, browbeats him about his bootlegging empire (Prohibition is in effect) and the still more ambitious criminal doings that made his fortune—Meyer Wolfsheim, the man who fixed the 1919 World Series, claims to have mentored him in the black arts. These painful revelations shock Daisy; in her distress she drives off in Gatsby’s car with Gatsby as her passenger, speeding off to the novel’s tragic denouement.

A remorseless pagan Fate seems to operate here. America’s favorite romantic classic ends with the cruel raw perfection of tragedy that sneers as it devastates. Accident rules the day, but accident in sardonic lockstep, and rash judgment does its bidding. “They were careless people, Tom and Daisy—they smashed up things and creatures and then retreated back into their money or their vast carelessness, or whatever it was that kept them together, and let other people clean up the mess they had made….” (Fitzgerald’s ellipsis). It was Gatsby who identified the seductive music in Daisy’s voice as “full of money.” His tragedy is that he conceived his ideal love in the need of big money because the woman he fell for could not endure the thought of life without a fortune. It was a losing proposition that F. Scott Fitzgerald knew from the inside out, and turned into an American masterpiece.