100 Years on, Why “The Great Gatsby” Remains Great

And why it’s F. Scott Fitzgerald’s best novel

Alexander Gil
Hooked on Books
11 min readAug 1, 2024

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Credit: Mathew Murphy and Evan Zimmerman

When someone asks me what my favorite book is, it almost feels like a copout to say The Great Gatsby — it’s like saying “Lincoln” if asked for your favorite president, or claiming “The Beatles” as your favorite band. Its obviousness just engenders an unavoidable degree of, well — banality.

I suspect, like other books cursed to the limbo of the high school educational circuit, that Gatsby to most people does not represent a meaningful work of literature, but a scarcely recalled, reluctantly slogged through homework assignment, one that, once completed, was enthusiastically put down and never picked up again. I’m embarrassed to admit that up until relatively recently I was one of these people. I mean, when you’re sixteen the last thing occupying real estate in your attention-assailed, image-obsessed, FOMO-driven brain is the story of a bunch of privileged, hard drinking Long Islanders from over a century ago. But upon revisiting the book in my late twenties, when I began reading fiction again for pleasure rather than obligation, I realized how much my sixteen year old eyes had missed.

As a long time claimant to the much extolled, arguably meaningful honor “The Great American Novel”, as well as being the tome virtually every American adolescent was forced to read in English class, Gatsby invites both widespread adoration and dismissal, the kind of love-it-or-hate-it sentiment usually reserved for sports teams or Nora Ephron films, or cilantro. Though I’m a fan, there are legitimate criticisms. Is a book centering on an affluent, straight white male protagonist still relevant in our modern age? Especially considering the wealth of wonderful books written by more recent, ethnically and sexually diverse authors? Admirers often cite Gatsby’s effectiveness as a compact, easily accessible rumination on the “American Dream” as the foremost quality justifying its abiding prominence in our culture — or at least our classrooms — but I’d venture much simpler, more fundamental defense: it’s a superbly written book, one far more complex than its brevity suggests.

Credit: Peter Harrington

F. Scott Fitzgerald is often lumped together with other expat writers of the 1920’s, dubbed the so-called “Lost Generation” by literary godmother Gertrude Stein, but the designation has always struck me as false. To read Fitzgerald is to recognize a writer that has more in common with Edith Wharton or Henry James than Ernest Hemmingway or James Joyce; the latter two examples being men who, by different but similarly radical avenues, treated prose with brutal indifference to the stuffy customs and conventions of their Victorian predecessors, and thus helped reinvent it in the process.

Fitzgerald, by contrast, was a lyrical writer, a poetical one, a true believing romantic not so much interested in reinventing prose as elevating it, refining it to a high, elegant shine. Given this predilection it’s unsurprising that he was an ardent admirer of the English romantic poets, most notably John Keats (one of the only recordings of Fitzgerald’s voice is from 1940, shortly before his death, of him reciting, from memory, Keat’s Ode to a Nightingale https://www.youtube.com/watch?v=fMKHwMGIVI8&t=13s). He took to heart Keats’s raison d’être of making language a living, breathing thing, infusing very word with movement and life and, at its best, a rhapsodic beauty that reverberates long after in the reader’s mind. One need read no further than this passage from Gatsby, a description of Tom Buchanan’s house, to see this influence at work:

“The lawn started at the beach and ran toward the front door for a quarter of a mile, jumping over sun-dials and brick walks and burning gardens — finally when it reached the house drifting up the side in bright vines as though from the momentum of its run.”

It’s simple, and that’s the point — the vividness, the movement, the poetry, all delivered in a condensed, facile style that, like all of Fitzgerald’s best writing, flows effortlessly from one sentence to the next without drawing attention to itself, so that the effect of its magic is cumulative, realized only after you’ve broken away from its spell.

It’s this quality that Gertrude Stein was probably thinking of when she praised Fitzgerald for being able to “write naturally in sentences” — a compliment that any writer knows indicates far more than its simplicity implies. This natural seeming proclivity for the written word was also, to anyone familiar with Fitzgerald’s writing process, a bit of a deception. While there’s no doubt he was born with a gift, the dude was also a grinder. Behind those pretty words — every dazzling, carefully crafted jewel of a sentence — there are exponential tons of excavations. Fitzgerald was his own harshest critic, no less a ruthless editor than Hemingway, and an obsessive curator of his work — often crafting extensive, near novel length outlines of his books before writing them. In other words, while gifted, he was a writer no different from any other, one who devoted long hours of labor to cultivating his craft.

F. Scott Fitzgerald. Credit: Roger-Viollet

It’s unfortunate then that throughout his life Fitzgerald was perceived by most critics as something of a literary lightweight, an author who chose to waste his innate talent in pursuit of remunerative awards in the “slicks”, with stories about “flappers” and teenage love, rather than stretch them in the pursuit of artistic greatness. Gatsby was a direct challenge to this charge; a consciously artistic achievement meant to dispel with the image of “F. Scott Fitzgerald: pop culture chronicler of the ‘Jazz Age’”, and hoist him to the pantheon literary greatness. In a letter written to his editor, Max Perkins, in July of 1922, a full three years before Gatsby’s publication, we see this ambition beginning to coalesce: “I want to write something new — something extraordinary and beautiful and simple + intricately patterned.” and, in another missive around the same time, we find both a statement of ambition and a bit of wry self-awareness: “…I shall write a novel better than any novel ever written in America, and become par excellence the best ‘second-rater’ in the world.” It was clear that from the start, Fitzgerald was staking his claim to artistic immortality on Gatsby.

Part of what elevates Gatsby above Fitzgerald’s other novels (he completed four during his lifetime), aside from its crystalline prose, is that it fixes the pesky structural and narrative problems that plagued his two previous books — hurdles that, with the exception of Gatsby, Fitzgerald would never quite clear throughout his life. While always excelling at producing luminous prose — a sentence to sentence fluency most authors would kill to have — when it came to novel length efforts Fitzgerald’s deficiencies in the broader realm of construction showed. To anyone who’s read This Side of Paradise, his splashy debut novel, this deficiency is glaring. Though there are passages that clearly indicate the arrival of a profound talent, the book is essentially a Frankenstein of disparate voices and formats, stitched awkwardly together to resemble a novel. His sophomore effort, The Beautiful and Damned, improved on these areas a little, but is still uneven, and, like much of Fitzgerald’s early work, prone to flights of purple, intellectually pretentious prose.

Gatsby does away with all of that. The book’s authorial voice is concise and effective, deftly shifting between past and present through the use of Nick Carraway, whose first person narration strikes the right balance between confidante and casual observer — a point of view allowing for an aura of mystery to build around its subject, enigmatic millionaire Jay Gatsby. By having Nick tell the story in retrospect, after the grisly culmination of events has already occurred, we also get a tale predominated by the foreboding presence of Fate. It’s this element — the question of whether or not we really direct the steering wheel of our destinies — that is arguably the central theme of Gatsby, and one that dovetails nicely with the notion of the “self-made man”, a concept at the heart of American Dream. Fate’s permeating presence, the sense that — like the star-crossed lovers in Romeo and Juliet — doom awaits Gatsby no matter how hard he tries to recapture Daisy’s love, adds a heightened sense poignancy to his quest, elevating it, and thus his character, to a nobility that surpasses the superficial glitz and glamor of the world he inhabits.

Close readers will also recognize the “intricate pattern” Fitzgerald was striving for in his conception of the novel, not only in it’s watertight construction (so hyper-designed is the plot that Gatsby and Daisy meet in the precise middle of it) but through the heavy deployment of symbols throughout. We have the enormous, omnipotent eyes of Dr. T.J. Eckleburg, watching God-like over the Valley of Ashes, where “ashes grow like wheat into ridges and hills” and men “move dimly and already crumbling through the powdery air”; there is the contrast between East Egg and West Egg — the patrician class vs. social climbers, the former embodied by Tom Buchanan, one of the best fictional villains ever written; and let’s not forget the famous green light, the embodiment of Gatsby’s hope, his eternal yearning for Daisy, of all the books symbols the most beautiful and enduring. Like his prose, which achieves meaning and beauty through the process of accretion, it’s Fitzgerald’s ability to skillfully and subtly weave these symbols throughout that imbue the novel with its poetic, almost mystical power.

Credit: Warner Bros.

And then of course there are the famous party scenes, which for casual readers is probably the thing they most associate with the book. I suspect, given that these passages take up a rather slim portion of the narrative (only two scenes in all), that the reason for their outsized spell on the public’s imagination is because it’s here we find Fitzgerald’s prose at its most incandescent. From his likening of partygoers to “trembling opals” and “scarcely human orchids”, to synesthesia-tinged phrases like “yellow cocktail music”, the scenes, with their gleeful exposition of bacchanalian excess, are saturated by a carnival-like profusion of color and light, a surface level magnificence that leaves an indelible mark on the reader’s imagination.

Over the years, there have been many dives into the profundities lurking beneath Gatsby’s sparkling surface. NPR book critic Maureen Corrigan, a professed Gatsby obsessive who’s read the novel upwards of fifty times, excavates all the ways in which water plays a meaningful role throughout the book: a symbol of baptismal purification, death, Gatsby’s eternal love for Daisy. There’s the restlessness we see in the novel — the restlessness of Tom and Daisy, the constant, twitchy movements of Gatsby (both literal and his incessant reaching to recapture the past) that some discern as an early exploration of PTSD, given both main characters are veterans of the first world war. It has even been picked up by some segments within the LGBTQ community as a proto-queer novel, based on the assumption that Nick’s character is a repressed homosexual. While I think this last reading goes beyond Fitzgerald’s original intent, it’s just one more example illustrating how much complexity the author managed to pack into so few words.

For this admirer, who’s now read the book at least twenty times (I intend to catch up with Ms. Corrigan one day), it’s Jay Gatsby himself, sparsely sketched as he is, that constitutes a large part of the novel’s enduring appeal. He’s kind of tacky, sure. He’s a bootlegger, check. But he is also a dreamer, a social striver, an unyielding optimist whose “extraordinary gift for hope”, as Nick puts it, insulates him from the corruptive influence of wealth and moral depravity of those surrounding him. Compared to the debauched characters he associates with, Gatsby remains pure.

It’s the death of this hope, the loss of those youthful allusions which inevitably succumb to the ignominies of age, that is the real tragedy of Gatsby — a sentiment captured so movingly in a passage near the novel’s end, after Gatsby has died, when Nick is ruminating on the final moments of his friend’s life:

“…he must have felt that he had lost the old warm world, paid a high price for living too long with a single dream. He must have looked up at an unfamiliar sky through frightening leaves and shivered as he found what a grotesque thing a rose is and how raw the sunlight was upon the scarcely created grass.”

Scott, Zelda, and Scottie in the south of France, 1924. Credit: Hulton Archive/Getty Images

Like so much of Fitzgerald’s work, the author has written his life into his art. Fitzgerald himself had remade his life in an effort to recapture the love of a woman (in his case Zelda Sayre), and it was in the midst of losing her — and to some extent his once glittering, wunderkind status as writer — that Gatsby was written. As a result the novel is saturated, above all things, by a profound sense of loss.

Fitzgerald famously once said “there are no second acts in American lives”, and yet his own life can be seen as evidence to the contrary. He reinvented himself once, early on with the breakout success of his debut novel, This Side of Paradise, and then again, after his untimely death at 44, when he went from forgotten relic of the “Jazz Age” to one of the most revered and influential novelists of the 20th century, a resurrection the likes of which Jay Gatsby would’ve no doubt applauded. Like Gatsby, Fitzgerald never stopped trying to reinvent himself (what snippets we have of his last, unfinished novel, The Last Tycoon, gives us tantalizing hints of the masterpiece that might’ve been), and that, to me at least, is the real beauty of The Great Gatsby — Gatsby’s striving even in the face of certain defeat, his retention of hope even when all plausible reason for its existence has ceased, “the doomed beauty of trying” as Maureen Corrigan aptly put it.

There is a passage from a John Keats poem, Endymion, that I’m often reminded of whenever I finish reading Gatsby. The passage is a meditation on the eternal quality of beauty, its everlasting perfection in a world where death and decay is the terminus toward which all things inevitably march. I think of it because Gatsby’s beauty, the mesmerizing power of its language, is a thing that seems to multiply with time, a quality it shares with all great works of art.

“A thing of beauty is a joy forever:

Its loveliness increases; it will never

Pass into nothingness; but will still keep

A bower quiet for us, and a sleep

Full of sweet dreams, and health, and quiet breathing.”

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