He died thinking he was a hack. Seriously. When F. Scott Fitzgerald suffered a fatal heart attack in 1940 in a quiet apartment in Hollywood, his final royalty check was measly, and The Great Gatsby—the book you likely struggled through in high school—was basically gathering dust in a warehouse. People had moved on. They thought he was a relic of a drunker, louder era that the Great Depression had rightfully killed off.
But history is weird.
Now, F. Scott Fitzgerald is the guy we look to when we want to understand the American Dream, or at least why it feels so hollow sometimes. He didn't just write stories; he lived the brand until it burned him alive. He was the king of the Jazz Age, a term he actually helped popularize, and he spent his life trying to outrun the fact that he was a middle-class kid from Minnesota trying to play dress-up with the old money elites of the East Coast.
The Myth of the Overnight Success
In 1920, Fitzgerald published This Side of Paradise. It was an instant explosion. One day he’s a struggling veteran who just got dumped by his socialite girlfriend because he was too poor, and the next, he’s the voice of a generation. He got the girl, too. Zelda Sayre, the "first American Flapper," married him a week after the book came out.
It sounds like a movie. It wasn't.
The reality of being an author like F. Scott Fitzgerald in the 1920s was a constant, grueling cycle of "writing for the checks." He would crank out short stories for The Saturday Evening Post just to fund a lifestyle he couldn't actually afford. He was getting paid roughly $4,000 per story at his peak—which is insane money for the time—but the booze, the travel, and the Ritz hotels ate it all.
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He once wrote that "an author ought to write for the youth of his own generation, the critics of the next, and the schoolmasters of ever after." He nailed that last part, though it took fifty years for the schoolmasters to catch up.
Why The Great Gatsby Actually Failed (At First)
You probably think The Great Gatsby was a hit. It wasn't. When it dropped in 1925, the reviews were... mixed, to put it politely. Some critics thought it was just a glorified crime novel. It sold fewer than 25,000 copies in his lifetime.
Compare that to the hundreds of thousands it sells every year now.
The genius of the book is something Fitzgerald lived: the "double vision." He was able to be inside the party, drinking the champagne and loving the glamour, while simultaneously standing outside the window judging everyone in the room. He called it the ability to "hold two opposed ideas in the mind at the same time and still retain the ability to function."
- Jay Gatsby represents the desperate hope of the self-made man.
- Tom Buchanan represents the casual cruelty of inherited wealth.
- Daisy Buchanan is the "golden girl" whose voice sounds like money.
Fitzgerald knew he was Gatsby. He was the striver who thought if he just got enough "stuff," he’d finally belong. He never did.
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The Zelda Factor: Muse or Saboteur?
You can’t talk about F. Scott Fitzgerald without talking about Zelda. Their marriage was a high-octane wreck. They were the "it" couple of New York and Paris, but behind the scenes, it was a mess of alcoholism, mutual infidelity, and eventually, Zelda’s tragic struggle with schizophrenia.
Honestly, it was toxic.
They stole from each other. Literally. Fitzgerald famously used Zelda’s own diaries as source material for his novels, particularly Tender Is the Night. Zelda, in turn, felt stifled and lashed out. By the 1930s, the party was over. Zelda was in and out of sanitariums, and Scott was drowning in gin and debt.
The "Crack-Up" and the Hollywood Years
By 1936, Fitzgerald was a "has-been." He wrote a series of essays called The Crack-Up for Esquire. They are heartbreakingly honest. He talked about how his vitality had just... evaporated. He described himself as a "cracked plate," the kind you keep in the cupboard but never use because it can't hold hot water.
People hated these essays at the time. His peers, like Ernest Hemingway, thought he was being a pathetic whiner.
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Hemingway and Fitzgerald had a legendary, complicated "frenemy" relationship. Hemingway was the tough guy; Fitzgerald was the sensitive one. Hemingway later trashed Scott in A Moveable Feast, portraying him as a weakling who couldn't handle his liquor or his wife. It was a low blow, especially since Scott had actually helped Hemingway get his start with the publisher Scribner’s.
Fitzgerald spent his final years as a "script doctor" in Hollywood. He hated it. He felt like a failure working on movies like Gone with the Wind (he was fired after two weeks) while trying to finish his last novel, The Last Tycoon. He died with that book unfinished.
Why He Still Matters in 2026
We live in an Instagram world. We spend our lives curating "the dream" while feeling like frauds on the inside. That is the core of F. Scott Fitzgerald’s work. He saw the "hollow core" of American consumerism a century before we had apps for it.
His prose is also just... better than everyone else's. Even if you hate the plots, you can't deny the music of his sentences. He would rewrite a single paragraph dozens of times to get the rhythm right. He didn't just tell you a character was sad; he told you their dreams were "borne back ceaselessly into the past."
How to Actually Read Fitzgerald Without Getting Bored
If you want to understand the man, don't just stop at Gatsby.
- Read the Short Stories: Specifically The Rich Boy or Winter Dreams. These are basically the blueprints for his bigger novels.
- Pick up Tender Is the Night: It’s messy and arguably too long, but it’s the most honest thing he ever wrote about his marriage and the "beautiful people" of the French Riviera.
- Check out the Letters: His letters to his daughter, Scottie, are full of surprisingly practical (and often cynical) advice about life and money.
- Watch for the "Double Vision": Whenever you read him, look for the moment where he stops being the party guest and starts being the judge.
Actionable Takeaways for History and Lit Buffs
If you're looking to explore the world of F. Scott Fitzgerald further, there are a few specific places to start that go beyond the classroom:
- Visit the Fitzgerald House in St. Paul: It’s a literal row house where he wrote his first hit. It’s a great reminder that he started as a normal kid with big dreams.
- The "Gatsby Curve": Economists actually use this term to describe the relationship between social mobility and inequality. It’s worth a Google if you want to see how his fiction matches modern economic reality.
- Support the Archives: The Princeton University Library holds the majority of his papers and original manuscripts. Their digital exhibits offer a raw look at his frantic editing process.
F. Scott Fitzgerald wasn't a saint, and he certainly wasn't a "success" by the standards of his final years. He was a flawed, brilliant, and deeply insecure man who happened to be able to write better than almost anyone in the English language. He showed us that the green light at the end of the dock is always further away than it looks—but we’re going to keep rowing toward it anyway.