F. Scott Fitzgerald: The Genius Behind The Great Gatsby

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On any list of the greatest American novels, there’s one book you can guarantee will be near the top: *The Great Gatsby*. It’s not just an acknowledged masterpiece; it’s one of the most influential things ever written. Its descriptions of wild jazz parties, bootlegging millionaires, and the beautiful and damned of New York have become shorthand for the entire Roaring Twenties. While Gatsby continues to exert a powerful hold over American culture, knowledge of its author has faded almost to the point of obscurity. That’s a pity because the life of F. Scott Fitzgerald is almost as fascinating as his most famous creation.

Born to an upper-middle-class family on a perpetual downward slide, Fitzgerald was a man tormented by his failings. In his eyes, he was never rich enough, tough enough, or manly enough. He tried to hide behind lavish parties, heavy drinking, and friendships with macho men like Ernest Hemingway. Yet while Fitzgerald would never be able to escape his sense of failure, that feeling would propel him to create some of the greatest prose in American history.

It’s a truism that everything comes down to perspective. You might be poor, useless, and alone, but if you’re used to being poor, useless, alone, and on fire, then things don’t look so bad. On the other hand, you might be from a connected family, go to private schools, mix with the beautiful and the rich, and still feel like a miserable failure. It’s in this latter category that F. Scott Fitzgerald fell.

Born Francis Scott Fitzgerald on September 24, 1896, in Saint Paul, Minnesota, Fitzgerald was the only son of an upper-middle-class family desperately trying to cling to that status. His father, Edward, was a failed store owner turned salesman who always seemed to be one wrong step away from getting fired, while his mother, Molly, although independently wealthy, came from a blue-collar Irish background. Fitzgerald was named after a famous distant cousin, Francis Scott Key, who wrote the “Star-Spangled Banner.”

Fitzgerald spent most of his young life between Saint Paul and New York State as Edward’s job forced the family to move. Although they always lived among the well-off, Fitzgerald was acutely aware from an early age that he didn’t quite belong. His father’s income was too precarious, and his mother’s background was too working-class. Although he would have seemed wealthy to most Americans, Fitzgerald always had the sense that his family were interlopers in this rich world. This feeling only increased when, in 1908, Edward finally lost his job. For a 12-year-old boy, it was like Armageddon. Fitzgerald later prayed, “Dear God, please don’t let us go to the poor house.” It was an easy request for the Almighty to grant; Molly still had her family’s money, and there were relatives who could pay for him to keep attending private schools. But when you’re 12, you don’t realize how lucky you are. You just hear the other kids joking about your deadbeat dad, see their expensive lives, and feel like an outcast.

This sense of always having one foot inside and one outside the world of the rich would one day drive Fitzgerald’s best writing. Socially, he was doing just fine; as a teen, Fitzgerald was relatively handsome and charming to a fault. Deadbeat dad or no, he still got invited to parties, made out with pretty girls, and even managed to get into Princeton in 1913 despite failing the admissions test. All his childhood, Molly had tried to make up for their family standing by telling her boy he was destined for important things. Now fate just seemed to be agreeing with her.

At Princeton, Fitzgerald joined the prestigious drama group, the Triangle Club, wrote witty sketches for campus magazines, and skipped class to attend literary parties. It was like Fitzgerald was play-acting his dream of what being wealthy must be like—a dream where you could flunk all of your studies and still coast by on your charm. Sadly, it was just a dream. Towards the end of his time at Princeton, Fitzgerald fell in love with a wealthy socialite named Zelda Sayre, but the relationship soon fell apart when he overheard her casually declare that poor boys shouldn’t think of marrying rich girls. For someone as obsessed with status as Fitzgerald, this comment was like all his nightmares coming true.

In 1917, it was clear he was about to flunk college, so he decided to leave before he was pushed. That year, Fitzgerald walked away from Princeton, leaving behind the glittering wealthy life he had chased for so long for a life of hardship and adventure in the army. In April, the U.S. declared war on Germany, and by 1918, huge numbers of American troops were being sent to the Western Front, among them F. Scott Fitzgerald.

In the last weeks before he was shipped to his training camp, Fitzgerald wrote letters to his family declaring that he was certain he would die in Europe. As the clock ticked down, he seemed to have gone from merely telling people this to actually believing it. In the officers’ club in New York, anyone might have noticed a short, handsome boy hunched over a typewriter, furiously pounding the keys. He was desperate to get something written before his death. The result was *The Romantic Egoist*, a barely disguised autobiographical take on Fitzgerald’s time at Princeton. It showed incredible promise, so much so that the publisher Scribner’s told him in the rejection letter that they would eagerly read anything he sent in the future.

In early 1918, he was shipped for training near Montgomery, Alabama. Since getting new recruits combat-ready was time-intensive, Fitzgerald would stay in the South for most of the year. That was fortunate because it gave him the chance to meet Zelda, the daughter of a state supreme court judge. Zelda possessed just about every quality Fitzgerald thought was lacking in himself: she was wealthy, confident, and unafraid of what people thought. She was also a party girl, able to drink even the hard-drinking Fitzgerald under the table. The pair met in July, and by September, Fitzgerald was writing in his diary the short yet loaded sentence: “Fell in love.”

Thankfully, he wouldn’t have to test that love in the nightmare of war. In November 1918, before Fitzgerald could be deployed, the Central Powers collapsed, ending World War I. Suddenly, the young man was free to leave the army, make a living, and marry his girl. He headed to New York City, determined to land a plum job as a journalist to impress Zelda. Instead, Fitzgerald found himself working at an advertising agency for a pittance. His one success during this period was writing the tagline for a laundry in Muscatine, Iowa: “We keep you clean in Muscatine.” Not exactly the stuff of literary greatness.

In 1919, Fitzgerald sold only a single short story that made him $30. As his professional life floundered, so did his love life. That year, Fitzgerald proposed to Zelda, only to be declined. Terrified he was losing yet another rich girl, he decided to gamble everything on that encouraging rejection letter from Scribner’s. At the end of the year, Fitzgerald quit his job, got drunk for three days straight, and then left NYC for Saint Paul. There, he loaded his typewriter, sat down, and furiously began rewriting *The Romantic Egoist*. It was a desperate hope that this time, with this rewrite, he would unleash his hidden masterpiece. In Fitzgerald’s case, it also happened to be true.

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Now, back to today’s video. If you were a literature fan in the 1920s, there would be only one F. Scott Fitzgerald book you were raving about—a book that defined the entire Jazz Age—and its name wasn’t *The Great Gatsby*. *This Side of Paradise* was the novel that turned Fitzgerald into a superstar. Broadly, its plot is no different from a gazillion other coming-of-age novels, but in its specifics, it was a revelation. This was the book that first brought the Roaring Twenties to popular imagination—a book that did for flapper girls and jazz artists what *Trainspotting* did for pill-popping Brits in 1999. The way the characters acted, dressed, talked, and experienced life were all real, all parts of what the new generation was experiencing as they shrugged off their parents’ values.

Published on March 26, 1920, it turned Fitzgerald overnight into the voice of his generation. Just 23, he was suddenly wealthy, fated, and adored by readers and critics alike. Just a week after the book debuted, Fitzgerald tied the knot with Zelda. No longer was he the poor boy standing outside the circles of the rich, looking helplessly in. For the first time in his life, Fitzgerald was the rich one.

You can probably guess how the future great Gatsby author dealt with becoming famous: by partying like he was starring in the Baz Luhrmann film of his own life. In the first half of the 1920s, the Fitzgeralds spent recklessly through bashes and, of course, drank like a pair of alcoholics. With *Paradise* a success, Fitzgerald was suddenly in demand from well-paying short story magazines, allowing him to top up his income at a moment’s notice. But even in these early days, there were already signs of trouble ahead. Fitzgerald was spending like an Italian government, throwing out way more money than he had coming in, forcing him to secure loans against future writing projects. That was all fine as long as he eventually wrote those books, but if he were to get writer’s block one day… well, yes, that was absolutely foreshadowing.

In late 1921, Zelda gave birth to their daughter, Scottie, and the family moved to the wealthy Long Island enclave of Great Neck. There, among the high-flying financiers, silent movie stars, and other literary celebrities, they lived out a grander vision of Fitzgerald’s Princeton days—a vision that would power his next novel. 1922’s *The Beautiful and the Damned* was a satire on the Jazz Age. Fitzgerald was meant to speak for a novel about excess and lusting after wealth. Today, it’s also considered his worst book—a flawed work that just about gets a pass thanks to his command of language. Still, it was good enough to keep the couple in the public eye, and they continued to lead their charmed lives, lives as charmed as those of the Princeton rich Fitzgerald had once obsessed over.

Yet even as he was living it, there must have been something about this life that bothered him. Around 1923, Fitzgerald began sketching ideas for a new novel—one that would expose the raw emptiness of Great Neck’s social bubble, even as he reveled in it. But it wouldn’t be possible to write while still living in this fine house, still drinking these fine cocktails, still partying with these powerful people. Back in 1921, the Fitzgeralds had briefly decamped to Europe, only to return when Zelda fell pregnant. Now, the war-shattered continent was looking less like another venue for partying and more like the perfect escape.

In 1924, the couple made their move. That year, America’s hottest literary superstar arrived on the French Riviera, ready to write his masterpiece. It was on this sun-drenched coast overlooking the blue waters of the Mediterranean that *The Great Gatsby* would soon be born. The story of a curious Midwesterner who moves to Long Island and settles next to the super-rich, super-mysterious Jay Gatsby, *The Great Gatsby* is one of those novels that everyone knows. It’s also one of those novels that manages to cram impossible amounts into a tiny word count. On its surface, it’s about Gatsby’s longing for the rich girl he can never have and the American elites who will always reject him, no matter how much money he makes. But it’s also a book about the USA’s hidden class system, about the power and limits of the American Dream, about the emptiness of Gatsby’s life, and the dark side of the Jazz Age. In short, it’s a great book—something in which you can find almost anything.

But that’s not how people saw it at the time. When *Gatsby* hit the shelves in 1925, most reviewers were flummoxed. “Fitzgerald’s latest: a dud,” ran one infamous headline. While other critics at least acknowledged the book’s lyricism, they still felt the story of the bootlegger Gatsby was too simple, too tawdry to earn the appellation “great.” Still, the novel did have its fans, especially in artistic and bohemian circles. One of those fans would soon become Fitzgerald’s greatest frenemy: Ernest Hemingway.

Hemingway was a man who almost never had a good word to say about any contemporary writing except his own. In 1925, he was still a lonely journalist living in Paris and working on his first real novel when he began to hear about this famous writer in town. Fitzgerald, too, had heard of Hemingway, both down on the Riviera and after he and Zelda moved to Paris. The two finally met one fine April day at the Dingo Bar, about two weeks after *Gatsby* was published. It was the beginning of literature’s greatest bromance and rivalry. As with Zelda, Fitzgerald seemed to see something in Hemingway that he lacked in himself: boundless confidence, physical strength, and a stack of stories from his war years. For his part, Hemingway, having read *Gatsby*, seemed to think Fitzgerald was just about the only other American writer worth a damn. It probably helped that they were both capable of putting away tremendous quantities of alcohol—a mutual interest that defined their friendship.

But it was a friendship that would benefit one half more than the other. With his connections, Fitzgerald was able to help Papa get *The Sun Also Rises* published at Scribner’s, promoting Hemingway’s literary career with more enthusiasm than his own. He also lent the younger man money to rush home when his father’s health collapsed and loaned him his Riviera villa when his sick son needed to recuperate. For his part, Hemingway openly admired Fitzgerald’s talent, telling him to have more confidence in his abilities. But he was also something of a massive jerk towards him. Never one to like being in another man’s shadow, Hemingway belittled Fitzgerald behind his back, spreading rumors that the *Gatsby* author was a “pansy.” He also openly hated Zelda and would later mercilessly eviscerate both of them in print. Hemingway’s posthumous account of his time in Paris, *A Moveable Feast*, paints Fitzgerald’s feet as “xenophobic, perpetually wasted, and scared his penis was too small to satisfy women.” I mean, why stick the knife in when you could just cut out his whole damn heart?

Despite its dark side, the two men’s friendship would keep up for several years, shaping their careers. But while Hemingway’s career was destined to spend the following decades reaching ever greater heights, Fitzgerald’s was almost already over. In just a few short years, he was going to transition from voice of his generation to forgotten, cracked-up, penniless alcoholic.

By the time Scott and Zelda quit Paris and returned to the Riviera, their relationship had settled into a state of extreme dysfunction. The two were arguing constantly—proper screaming arguments that would end with Zelda grabbing her things and leaving, vowing never to return, only to come back that same night. The more they argued, the more Fitzgerald drank, until it became clear he wasn’t a party animal so much as a full-blown alcoholic. While there’s a romantic myth attached to writers and alcohol, the reality of Fitzgerald was that his addiction was devastating. He began to suffer writer’s block, unable to work on his follow-up novel to *Gatsby*. Desperate to get something on the page, he resorted to stealing passages from Zelda’s diary. While recent scholarship has disproved the theory that Fitzgerald was essentially passing off Zelda’s work as his own—seriously, Zelda wrote no more of *Gatsby* than Dan Brown wrote of *Infinite Jest*—it was still a crappy thing to do.

But as bad as things were getting for Fitzgerald, they were getting worse for Zelda. Throughout her life, Zelda had struggled with mental illness. Although she was diagnosed with schizophrenia, a modern psychiatrist would probably label her bipolar. She certainly had the dizzying highs and the devastating lows. Starting around 1929, those lows got even lower. After a brief stint back in America, the couple returned to France, where Zelda began to exhibit extreme obsessive behavior, especially around her ballet lessons. While this might sound somewhat harmless, it masked a serious problem. That year, Zelda suffered her first major breakdown—a collapse that led to her being placed in an institution.

At the same time, Fitzgerald’s physical health gave out, the latest effect of his alcoholism. It’s possible that the couple could have ridden out the twin crises had it not been for a third crash—this time one that would be heard around the world. The Wall Street Crash in October 1929 heralded the dawn of the Great Depression. It also threw into sharp relief just how much money Fitzgerald had borrowed against future books—books he was now incapable of writing—just as Zelda’s medical bills were starting to mount. The Fitzgeralds abandoned Europe for good in 1931. At the time, Zelda seemed to be recovering, but another breakdown the