In the glittering wreckage of the American Dream, F. Scott Fitzgerald found his literary gold mine. With prose as intoxicating as bootleg gin and as fragile as champagne bubbles, he captured the Jazz Age's beautiful excess and inevitable hangover in masterpieces like The Great Gatsby. His stories shimmer with wealth and desire while exposing the hollow promises lurking beneath society's most dazzling surfaces—a cocktail of beauty, longing, and disillusionment that continues to intoxicate readers nearly a century later.
Did you know? F. Scott Fitzgerald died in 1940 believing himself a failure. The Great Gatsby had sold fewer than 25,000 copies during his lifetime and was largely forgotten. It wasn't until World War II—when the Armed Services Editions distributed free copies to soldiers—that Gatsby found its audience. Today it sells over 500,000 copies annually and is considered one of the greatest American novels ever written. Fitzgerald's redemption came too late for him to witness it.
These writers were Fitzgerald's contemporaries and competitors, revolutionizing literature alongside him. They shared his commitment to breaking traditional narrative forms while capturing the post-World War I disillusionment that defined their generation.
Hemingway was Fitzgerald's friend, rival, and polar opposite in style. Where Fitzgerald adorned his sentences with lyrical excess, Hemingway stripped his prose to the bone—creating the famous "iceberg theory" where ninety percent of the story's meaning lurks beneath the surface. Yet both writers captured the same Lost Generation wandering through European cafes and Spanish bullfights, searching for meaning in a world shattered by war.
His novel The Sun Also Rises follows Jake Barnes and Lady Brett Ashley through a haze of Parisian parties and Pamplona's running of the bulls—a group of beautiful, damaged expatriates drinking to forget wounds both visible and invisible. Like Gatsby, it's a story of unrequited love and people trying desperately to feel alive in a world that's left them emotionally numb.
Faulkner took Fitzgerald's interest in American decay and pushed it into gothic, stream-of-consciousness territory. While Fitzgerald chronicled the North's Jazz Age excess, Faulkner dissected the South's haunted aristocracy—families collapsing under the weight of history, racism, and their own delusions of grandeur. His prose is dense, challenging, and rewards patient readers with profound psychological insight.
The Sound and the Fury examines the Compson family's decline through fragmented, non-linear narratives—each section revealing how the past poisons the present. Like the Buchanans in Gatsby, the Compsons are trapped by privilege they no longer deserve.
Woolf shared Fitzgerald's modernist project but approached it from a radically different angle. Instead of Jazz Age parties, she explored the interior landscapes of consciousness itself—the way a single day contains multitudes, how memory and identity blur and shift. Her characters attend elegant parties too, but Woolf shows us the thoughts flickering behind polite conversation.
Mrs. Dalloway follows Clarissa Dalloway through a single June day in London as she prepares for a party. The novel moves fluidly between past and present, revealing how our younger selves haunt us—a theme Fitzgerald understood intimately when he wrote "So we beat on, boats against the current, borne back ceaselessly into the past."
Literary Frenemies: Hemingway and Fitzgerald's friendship was as complicated as any Fitzgerald novel. They met in Paris in 1925, and Hemingway initially admired Fitzgerald's talent. But Hemingway later turned cruel, mocking Fitzgerald's drinking and calling his work sentimental. In A Moveable Feast, Hemingway wrote scathingly about Fitzgerald—but also admitted he was "the most talented writer of our generation." Fitzgerald, in turn, recognized Hemingway's genius while privately resenting his success. Their relationship perfectly embodied the competitive, self-destructive artist culture they both wrote about.
The Social Satirists & Class Observers
These authors share Fitzgerald's surgical precision when dissecting high society's hypocrisies, examining how money, class, and social expectations corrupt human relationships and individual freedom.
If Fitzgerald was the chronicler of 1920s New York society, Edith Wharton documented the Gilded Age aristocracy that preceded it—the old money families who looked down on Gatsby's flashy new wealth. She wrote with devastating precision about the rules, rituals, and restrictions that governed high society, showing how social conventions could destroy lives as surely as any tragedy.
The Age of Innocence (which won the Pulitzer Prize before Fitzgerald was even considered for one) follows Newland Archer, trapped between duty to his respectable fiancée and passion for the unconventional Countess Olenska. Like Gatsby reaching for the green light, Archer reaches for a life he can never have—doomed by the very society that shaped him.
Parker was Fitzgerald's contemporary and fellow Jazz Age chronicler, but she brought a wicked wit and feminist edge to her observations of 1920s Manhattan society. Her short stories are masterclasses in dark humor, revealing the desperate loneliness beneath fashionable parties and witty repartee. She knew the same crowd Fitzgerald did—and skewered them with precision.
Laments for the Living collects her savage, funny stories about love, loss, and the performative lives of the sophisticated set. These are the people at Gatsby's parties—the ones who show up drunk and leave drunker, laughing too loudly to cover the emptiness.
Waugh is essentially the British Fitzgerald—an aristocratic satirist who wrote gorgeous, melancholy novels about beautiful people making terrible decisions. He had the same gift for capturing doomed romance and the particular sadness of Oxford and country estates as Fitzgerald had for Princeton and Long Island mansions.
Brideshead Revisited is his masterpiece: a story of obsessive love, Catholic guilt, and the slow decline of English aristocracy, narrated by Charles Ryder looking back on his lost youth. "I have been here before," he says of Brideshead, and the novel explores the same nostalgic longing that Fitzgerald perfected—that sense that the past was more vivid, more meaningful, than the compromised present.
Capote inherited Fitzgerald's elegant style and interest in beautiful outsiders navigating high society. His characters—like Holly Golightly—are performers, creating glamorous personas to mask loneliness and trauma. He understood, as Fitzgerald did, that the most interesting people at the party are often the ones who don't quite belong there.
Breakfast at Tiffany's gives us Holly Golightly, a New York socialite whose charm and sophistication barely conceal her vulnerability and rootlessness. Like Gatsby, she's invented herself, fleeing a past she won't discuss. Like Daisy, she's ultimately unknowable, a beautiful illusion that vanishes when examined too closely.
American Dream Deconstructors
Fitzgerald's greatest theme was the American Dream's seductive promise and inevitable betrayal. These authors continue that examination across different eras and social landscapes, showing how each generation discovers that dream is a beautiful lie.
If Fitzgerald showed the American Dream's failure from the top of society, Steinbeck showed it from the bottom. While Gatsby chased Daisy through mansion parties, Steinbeck's characters chased survival through dust storms and labor camps. But both writers understood that America promises more than it delivers, particularly to those who believe in it most desperately.
The Grapes of Wrath follows the Joad family from Oklahoma's Dust Bowl to California's promised land—which turns out to be exploitation, poverty, and broken promises. It's Gatsby's green light relocated to California and revealed as a mirage.
Williams brought Fitzgerald's themes of illusion and disillusionment to the American South, creating characters who cling to faded glamour and impossible dreams. His plays are essentially Fitzgerald novels translated to the stage—gorgeous language in service of tragic characters who can't face reality.
A Streetcar Named Desire gives us Blanche DuBois, a fallen Southern belle clinging to memories of aristocratic grandeur while living in a New Orleans slum. Like Gatsby, she's constructed an elaborate fiction about her past. Like Daisy, she's ultimately destroyed by forces she can't control.
Yates is the 1950s Fitzgerald—the chronicler of how the American Dream curdled in suburban Connecticut, where the Gatsbys settled down and discovered that marriage, mortgage, and respectability were their own kind of trap. His characters are dying of quiet desperation in split-level houses, realizing too late that they've sacrificed everything meaningful for comfort and conformity.
Revolutionary Road follows Frank and April Wheeler, a suburban couple convinced they're different from their neighbors—more sophisticated, more authentic, more alive. They're wrong, of course, and Yates dissects their delusions with Fitzgeraldian precision. This is what happened to Gatsby's dream after it moved to the suburbs.
Didion brought Fitzgerald's themes to 1960s California, examining how the American Dream fragments completely in Hollywood and the desert. Her characters drift through swimming pools and canyon parties, emotionally numb, morally untethered, watching the culture collapse around them. She writes with Fitzgerald's elegance but Hemingway's spare brutality.
Play It as It Lays follows Maria Wyeth, an actress in Los Angeles, as she drives aimlessly on freeways, has meaningless affairs, and tries to feel something—anything. It's Gatsby's disillusionment relocated to the West Coast and stripped of romance entirely. The dream isn't just dead; it never existed.
💔 Fitzgerald and Zelda
The Original Toxic Romance: Fitzgerald's marriage to Zelda Sayre was the real-life model for his doomed romances. They met in 1918; she refused to marry him until he was successful. When This Side of Paradise became a bestseller, she agreed. Their marriage was glamorous, passionate, and catastrophic—marked by affairs, alcoholism, mental illness, and mutual destruction. Fitzgerald mined their relationship ruthlessly for material (Zelda complained he was stealing her life for his novels), while Zelda's own literary ambitions were eclipsed by his fame. Their story is as tragic as any Fitzgerald wrote—proof that he understood doomed love because he lived it.
Contemporary Heirs to Fitzgerald
These modern authors have inherited Fitzgerald's legacy, bringing his themes of class, privilege, obsession, and disillusionment to contemporary settings while maintaining his commitment to beautiful prose and complex characterization.
Tartt writes the Gatsby story for the 21st century—wealthy, charismatic young people making terrible decisions at elite institutions, narrated by an outsider seduced by their glamour. She has Fitzgerald's gift for making privilege simultaneously attractive and repulsive, for showing how obsession leads to tragedy.
The Secret History follows Richard Papen, a California scholarship student who falls in with an exclusive group of classics students at a Vermont college. Like Nick Carraway, he's drawn into their world, seduced by their sophistication and beauty—and witnesses the murder that results from their sense of being above conventional morality. This is Gatsby if Nick had helped cover up Myrtle's death.
Towles is perhaps the most Fitzgeraldian contemporary writer—devoted to elegance, social observation, and characters navigating class boundaries in glittering cities. His prose has the same careful beauty, his eye for social detail is equally sharp, and he shares Fitzgerald's romantic temperament tempered by realistic understanding of how society works.
Rules of Civility is deliberately Gatsbyesque: set in 1938 New York, it follows Katey Kontent as she moves from a boarding house to high society, drawn to the charismatic, mysterious Tinker Grey. Like Gatsby, it's about reinvention, class mobility, and the price of admission to gilded worlds. Towles even includes a car accident.
Eugenides writes about American suburbs with the same fascinated horror Fitzgerald brought to West Egg—finding mythology and tragedy in seemingly ordinary communities. He shares Fitzgerald's interest in how American dreams destroy the people who pursue them, and how memory transforms the past into something more beautiful and more painful than it ever was.
The Virgin Suicides is narrated by a group of boys obsessed with the five Lisbon sisters—beautiful, mysterious, ultimately unknowable, like Daisy Buchanan multiplied. The novel examines masculine obsession, idealized femininity, and suburban decay with Fitzgerald's same mixture of beauty and melancholy. The past haunts these narrators as powerfully as it haunted Gatsby.
McCullers shares Fitzgerald's profound understanding of loneliness—particularly the loneliness that persists in crowds, at parties, surrounded by people. Her characters are outsiders yearning for connection they can't articulate, isolated by circumstance and their own inability to communicate what they feel. It's Fitzgerald's emotional landscape relocated to the South and stripped of glamour.
The Heart is a Lonely Hunter portrays a deaf man in a Southern town who becomes the confessor for various lonely, desperate people—each pouring their hearts out to someone who can't fully understand them. It's a darker vision than Fitzgerald's, but equally concerned with failed connection and the impossibility of truly knowing another person.
Your Fitzgerald Reading Journey
📖 Suggested Reading Paths
The Complete Modernist Experience: Start with Hemingway's The Sun Also Rises → Woolf's Mrs. Dalloway → Faulkner's The Sound and the Fury. See how Fitzgerald's contemporaries tackled the same post-war disillusionment with radically different styles.
The High Society Tour: Begin with Wharton's The Age of Innocence (Gilded Age) → Fitzgerald's The Great Gatsby (Jazz Age) → Waugh's Brideshead Revisited (British aristocracy) → Towles' Rules of Civility (1930s). Watch the American upper class evolve and decay across generations.
The American Dream Autopsy: Read Fitzgerald's The Great Gatsby → Steinbeck's The Grapes of Wrath → Yates' Revolutionary Road → Didion's Play It as It Lays. Trace how the dream dies from the 1920s through the 1960s, across different American landscapes.
The Contemporary Gatsby Experience: Try Tartt's The Secret History → Eugenides' The Virgin Suicides → Towles' Rules of Civility. Modern writers reimagining Fitzgerald's themes for contemporary readers.
The Jazz Age Deep Dive: Read Fitzgerald alongside his contemporaries: Dorothy Parker's stories, Hemingway's The Sun Also Rises, and then jump forward to Capote's Breakfast at Tiffany's to see how the sensibility evolved.
🎯 By What You Loved Most About Fitzgerald
If you loved the prose style: Evelyn Waugh, Donna Tartt, and Amor Towles write with similar elegance and attention to language.
If you loved the tragedy: Tennessee Williams, Richard Yates, and Carson McCullers deliver equally devastating emotional punches.
If you loved the social satire: Edith Wharton, Dorothy Parker, and Waugh dissect class and privilege with surgical precision.
If you loved the doomed romance: Waugh's Brideshead Revisited, Tartt's The Secret History, and Capote's Breakfast at Tiffany's feature equally impossible loves.
If you loved the American Dream themes: Steinbeck, Yates, and Didion continue Fitzgerald's interrogation of American mythology.
If you loved the narrator's perspective: Tartt's Richard Papen and Eugenides' collective narrators echo Nick Carraway's position as fascinated outsider.
⚡ Quick Recommendations
Easiest Entry Point: Hemingway's The Sun Also Rises—accessible style, same themes, shorter than most Faulkner.
Most Like Gatsby: Waugh's Brideshead Revisited or Tartt's The Secret History—similar structure, tone, and tragic trajectory.
Most Challenging: Faulkner's The Sound and the Fury or Woolf's Mrs. Dalloway—experimental, demanding, rewarding.
Hidden Gem: Yates' Revolutionary Road—criminally underread despite being a masterpiece of American disillusionment.
For Short Story Lovers: Dorothy Parker's collections—perfect distillations of Jazz Age wit and heartbreak.
✍️ Fitzgerald's Writing Process
The Craft Behind the Beauty: Fitzgerald was a meticulous reviser who wrote and rewrote obsessively. The Great Gatsby went through extensive revisions—he was still making changes to the galleys, adding the now-famous final line ("So we beat on, boats against the current...") at the last possible moment. He kept detailed notebooks tracking phrases he liked, overheard dialogue, and character observations, mining them for his fiction. His seemingly effortless prose was actually the result of painstaking craft—he once said, "All good writing is swimming under water and holding your breath."
These fifteen authors represent different facets of Fitzgerald's literary DNA. Some share his prose style, others his themes, still others his social milieu or tragic sensibility. What unites them is a commitment to examining the gap between American promises and American reality, between the lives we dream of and the lives we actually live, between the beautiful surface and the hollow core beneath.
Fitzgerald died young, alcoholic, and convinced he'd failed. But his legacy lives on in every writer who examines class and desire, every novel about characters reaching for something just out of reach, every sentence that achieves the difficult balance between beauty and truth. These fifteen authors are his literary descendants, whether they acknowledge it or not—proof that Gatsby's green light still shines across the water, still pulls writers toward it, still promises something just beyond our grasp.
— F. Scott Fitzgerald