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F. Scott Fitzgerald wrote four complete novels, left a fifth unfinished, and published 164 short stories in his lifetime. He died in 1940 at 44, believing himself a failure. The Great Gatsby had sold modestly on publication in 1925; it was only after his death, when the US Army distributed hundreds of thousands of copies to soldiers in World War II, that it became the novel everyone has read. But Fitzgerald is far more than one novel — the heartbroken beauty of Tender Is the Night, the raw ambition of This Side of Paradise, the finest of his short stories — deserves as much attention. This is everything he wrote.
By Lisanne Swart · 9 books · Literary Fiction · Jazz Age · Updated August 2026
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F. Scott Fitzgerald and the Jazz Age he named and outlived
A look at the life behind the novels — Princeton, Zelda, the Riviera, and the long decline that shadowed his last decade.
The novels
Novel · Debut
This Side of Paradise
Fitzgerald’s first novel, written when he was 23 and published when he was 24. It follows Amory Blaine — charming, self-involved, uncertain — through Princeton, a series of love affairs, and the early aftermath of World War I. The book is loosely autobiographical and unapologetically young: Amory’s flaws are Fitzgerald’s flaws, barely disguised, examined with the kind of fascinated self-regard that only the very young can sustain. It was an instant bestseller. The money it earned allowed Fitzgerald to marry Zelda Sayre, who had broken off their engagement partly because he couldn’t support her. The publication of this novel is where the whole story begins.
This Side of Paradise is not Fitzgerald at his best — the prose is uneven, the structure loose, the philosophy undergraduate. But it is Fitzgerald at his most nakedly ambitious, and reading it alongside The Great Gatsby shows exactly what he learned in five years and how he learned it.
Novel
The Beautiful and Damned
Anthony Patch is the handsome, Harvard-educated grandson of a moralistic millionaire. His wife Gloria is beautiful, reckless, and entirely certain that beauty is all one needs. Together they wait for Anthony’s inheritance while slowly, methodically destroying themselves through parties, alcohol, and mutual recrimination. The novel is a portrait of a marriage collapsing and a generation squandering its promise — darker and more controlled than This Side of Paradise, with passages of painful accuracy about what it feels like to watch yourself deteriorating and not be able to stop.
The most underread of Fitzgerald’s novels and in some ways the most honest. It is largely about Zelda and Scott’s own marriage, thinly disguised — the charm that conceals emptiness, the mutual enabling, the way two people can make each other worse.
Novel · MasterpieceOn my shelf
The Great Gatsby
Nick Carraway moves to Long Island in the summer of 1922 and becomes drawn into the world of his neighbour Jay Gatsby — mysterious, extravagant, throwing parties he doesn’t attend for a woman he hasn’t spoken to in five years. The novel is about desire and self-invention and the American myth that the past can be undone if you want it enough. Fitzgerald wrote it in nine months on the French Riviera. It is 180 pages. It has sold over 25 million copies.
I have it on my shelf and return to it regularly. What makes The Great Gatsby endure is not the plot — which is simple — but the prose, which does something on almost every page that you cannot quite account for until you have read it several times.
→ Read my full thoughts on The Great Gatsby
→ Books like The Great Gatsby
Novel · Late Masterpiece
Tender Is the Night
Dick Diver is a brilliant American psychiatrist living on the French Riviera with his wife Nicole, a former patient he fell in love with and cured and married. Over the course of the novel — which spans the late 1910s to the early 1930s — Dick’s confidence erodes, his career collapses, and the marriage that was built on his strength gradually inverts. Fitzgerald worked on it for nine years. It received mixed reviews on publication and sold poorly.
The novel Fitzgerald’s admirers argue about most. Some consider it his greatest work — richer and more psychologically complex than Gatsby. It is a flawed masterpiece, and the flaws are part of what makes it moving: a man writing about his own disintegration while it was happening.
Novel · Unfinished · Posthumous
The Love of the Last Tycoon
Fitzgerald’s fifth and final novel, left unfinished at his death in December 1940 from a heart attack. He had completed roughly half the book, which follows Monroe Stahr — a powerful Hollywood producer modelled on Irving Thalberg — through a love affair that threatens his professional dominance. Edmund Wilson edited and published the fragment in 1941. A more complete scholarly edition, The Love of the Last Tycoon: A Western, was published in 1993.
Approach it as a fragment rather than a failed novel and it is extraordinary. The tragedy is not just that he died before finishing it, but that the existing pages show exactly what the finished book would have been.
Short Stories · Collection 1
Flappers and Philosophers
Fitzgerald’s first short story collection, published the same year as This Side of Paradise. Eight stories including “Bernice Bobs Her Hair,” “The Ice Palace,” and “The Offshore Pirate.” The stories are set among the young, wealthy, and restless — flappers and their admirers, debutante balls and country clubs — and they established the social world that Fitzgerald would spend his career examining.
The essential story here is “The Ice Palace” — a story about the incompatibility of different American worlds told through temperature and architecture. “Bernice Bobs Her Hair” is the most widely anthologised and earns its reputation.
Short Stories · Collection 2
Tales of the Jazz Age
The second collection, published the same year as The Beautiful and Damned. Eleven stories including “The Curious Case of Benjamin Button” — the reverse-aging fantasy later adapted by David Fincher — and “May Day,” a long story about a violent evening in New York in 1919. The collection gave the era its name: it was Fitzgerald who coined “Jazz Age,” and this book is where the term first appeared in a title.
“May Day” is the masterpiece here — long, novelistic, structurally ambitious, and almost never discussed alongside Fitzgerald’s best work. It should be.
Short Stories · Collection 3
All the Sad Young Men
Published one year after The Great Gatsby, this collection of nine stories is widely considered his best. It includes “Winter Dreams” — often described as the first draft of The Great Gatsby — and “The Rich Boy,” which opens with one of the most quoted sentences in American literature: “Let me tell you about the very rich. They are different from you and me.”
Start here if you want to understand Fitzgerald as a short story writer. “Winter Dreams” and “The Rich Boy” together cover the same territory as The Great Gatsby, but from different angles and with different resolutions.
Short Stories · Collection 4
Taps at Reveille
Fitzgerald’s fourth and final short story collection, published the year after Tender Is the Night. Eighteen stories including the four Basil Duke Lee stories and the three Josephine Perry stories. The collection also contains “Babylon Revisited,” which many critics consider the finest short story Fitzgerald ever wrote.
“Babylon Revisited” is the place to end with Fitzgerald’s short fiction — an American in Paris trying to reclaim his daughter after alcoholism, written as Fitzgerald’s own life was following that exact trajectory. It is the most honest thing he wrote.
→ My best fiction books of all time — Fitzgerald’s place in the canon
Where to start with F. Scott Fitzgerald
If you have never read him
→ Start with The Great Gatsby. It is 180 pages. It will take you an afternoon. And it earns its reputation in a way that few canonical novels do — not because English teachers assign it but because the prose is genuinely extraordinary and the argument underneath it still holds.
If you want to understand where Gatsby came from
→ Read “Winter Dreams” from All the Sad Young Men before or after The Great Gatsby. Fitzgerald wrote the same story three times — “Winter Dreams,” The Great Gatsby, and “The Rich Boy” — and each version shows you something the others don’t.
If you want the novel that his admirers argue is his actual best work
→ Tender Is the Night. Darker, messier, more personally painful than Gatsby, and in some ways more true. Read it after Gatsby, not before.
If you want his finest short story
→ “Babylon Revisited” in Taps at Reveille. It is the story where the glamour is entirely gone and what’s left is something much more honest and harder to look at.
If the Jazz Age world draws you — the parties, the excess, the beauty that conceals rot
→ My books like The Great Gatsby reading list has the natural successors. And my best fiction books of all time list places Fitzgerald in the broader canon.
If the obsession theme is what stays with you — the pursuit of an ideal that was never real
→ My books about obsession reading list takes that further. Fitzgerald practically invented the literary template for romantic obsession as self-destruction.
Frequently asked questions about F. Scott Fitzgerald’s books
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Books About Obsession
The pursuit of an ideal that was never real.
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Every Booker Prize Winner Since 1980
More prize-worthy literary fiction to explore.
From the bookshelf
“So we beat on, boats against the current, borne back ceaselessly into the past.” — F. Scott Fitzgerald
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