It was not, one assumes, the kind of review F. Scott Fitzgerald had hoped for.

Writing in the Baltimore Evening Sun in May 1925, H. L. Mencken dismissed The Great Gatsby as “a glorified anecdote” plagued by trivial plot devices and poorly drawn characters who, apart from the eponymous protagonist, were “mere marionettes.” And yet, while Mencken assured readers that Gatsby was “not to be put on the same shelf” with Fitzgerald’s debut novel This Side of Paradise (1920), he lauded the 28-year-old’s maturation as a prose stylist: “What gives the story distinction is something quite different from the management of the action or the handling of the characters; it is the charm and beauty of the writing.” 

Thus, in a single sentence, Mencken explains why it has proven impossible to replicate The Great Gatsby in film. The latest attempt, directed last year by Baz Luhrmann and starring Leonardo DiCaprio, inspired Gatsby-themed clothing and jewelry lines, as well as all manner of Jazz Age parties. But amid the celebration of Roaring Twenties chic, the quality of the movie seemed almost beside the point. For the record, I enjoyed it—despite its wholly predictable (and mostly unavoidable) shortcomings. But its limitations help us understand both the timeless appeal of Fitzgerald’s masterpiece and the enduring confusion over its meaning.

Nine decades after Gatsby’s publication, we are still awed by Fitzgerald’s gorgeous turns of phrase, his lyrical descriptions of the mundane, his knack for delivering profound observations in astonishingly concise language. As Mencken wrote: “There are pages so artfully contrived that one can no more imagine improvising them than one can imagine improvising a fugue.”

So if we’re ranking novels purely on the elegance of their prose, Gatsby is second to none. That’s one reason why it presents such an insuperable challenge to Hollywood. Consider this passage: “Americans, while occasionally willing to be serfs, have always been obstinate about being peasantry.” How could any filmmaker convey the meaning of those 14 words? With his trademark brevity, Fitzgerald makes a provocative statement about mobility and migration, and would surely have agreed with V. S. Pritchett’s assertion, in 1941, that “movement, a sense of continual migration, is the history of America.” Indeed, Pritchett might as well have been summarizing Gatsby’s dominant theme. (As it happens, he was writing about Huckleberry Finn.) 

The Great Gatsby is preoccupied with migration: the movement of its principal characters from West to East; the re-migration of the narrator, Nick Carraway, back to the West; the migration of Gatsby’s mentor Dan Cody, a millionaire Western prospector who “brought back to the eastern seaboard the savage violence of the frontier brothel and saloon”; even the 17th-century migration of Dutch sailors to the New World. There is also the extended metaphor of the nouveau riche West Egg (where Gatsby lives) and the aristocratic East Egg (where Tom and Daisy Buchanan reside). To further underscore the centrality of migration, Nick recalls traveling home for Christmas from boarding school and college. As his westbound train rode through Wisconsin,

A sharp wild brace came suddenly into the air. We drew in deep breaths of it as we walked back from dinner through the cold vestibules, unutterably aware of our identity with this country for one strange hour before we melted indistinguishably into it again.

Nick’s memory of “thrilling, returning trains” is among the most beautifully crafted passages in a book full of such passages. But of course, you wouldn’t have known it from the Baz Luhrmann film, which omitted so many of Gatsby’s narrative gems. To be sure, only so much narration can be packed into a 143-minute movie. Yet without Fitzgerald’s commentary, delivered in Nick’s voice, it’s easy to forget or misinterpret what the novel is really about. If The Great Gatsby were simply a tragic histoire d’amour, glittered with opulent party scenes, it would hardly have achieved its present canonical status. No, Gatsby belongs in the pantheon for two reasons: the magic of its prose and its peerless exploration of American identity.

Which prompts another question: What, exactly, was Scott Fitzgerald saying about the American Dream? He was clearly influenced by Frederick Jackson Turner’s frontier thesis, first presented in a symposium at the 1893 Columbian Exposition in Chicago, and later published in a 1920 collection of essays. Turner believed that   

American social development has been continually beginning over again on the frontier. This perennial rebirth, this fluidity of American life, this expansion westward with its new opportunities, its continuous touch with the simplicity of primitive society, furnish the forces dominating American character.

If Turner was correct, then 1890—the year Census Bureau officials declared that the United States no longer had a “frontier”—marked a watershed. Throughout Gatsby, Fitzgerald connects the frontier with America’s historic capacity for reinvention, implying that the absence of a frontier means diminished possibilities. As UCLA’s Richard Lehan has noted, even the name of Gatsby’s mentor (Dan Cody) “suggests the beginning and end of the frontier,” a marriage of Daniel Boone and Buffalo Bill Cody. 

During his final visit to Gatsby’s Long Island mansion, Nick contemplates a time when all America represented the frontier, when European seafarers encountered “a fresh, green beast of a new world.” Both he and Gatsby are wistful for their own Lost Edens. Gatsby believes that marrying Daisy—reaching the green light—will consummate his dream. But Nick takes a different view, informing us that Gatsby’s dream “was already behind him, somewhere back in that vast obscurity beyond the city, where the dark fields of the republic rolled on under the night.” Unlike his West Egg neighbor, Nick recognizes the impossibility of repeating the past, but he also appreciates Gatsby’s “extraordinary gift for hope.” While Jay Gatsby epitomizes “everything for which I have an unaffected scorn,” the onetime James Gatz “turned out all right at the end.”

In that sense, Nick’s contradictory feelings about Gatsby reflect Fitzgerald’s paradoxical attitude toward the American Dream. He certainly had a romantic attachment to his country’s founding ethos. In a 1929 short story entitled “The Swimmers,” he captured the abstract nature of Americanism: “France was a land, England was a people, but America, having about it still that quality of the idea, was harder to utter. .  .  . It was a willingness of the heart.” Years later, Fitzgerald asserted that American history “is the history of all aspiration,” making it “the most beautiful history in the world.” But he also lamented the gap in America between aspiration and reality. He feared that the aboriginal American Dream—the dream of Dutch sailors and westward pioneers—had become unattainable, but he admired those quixotic souls who still pursued it. “The test of a first-rate intelligence,” he wrote in 1936, “is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function. One should, for example, be able to see that things are hopeless and yet be determined to make them otherwise.”

Such nuance does not easily translate into cinema. So it’s no surprise that Baz Luhrmann’s Gatsby avoided grappling with any of the Big Questions raised by the novel. It dwelt, instead, on lesser themes appealing to mass audiences: lost love, hedonism, Jazz Age excess. The result was decent entertainment, without evidence of its author’s underlying message about America. Fitzgerald wanted The Great Gatsby to be “a consciously artistic achievement.” And it is, in literary terms. Just not for the movies.

Rachel DiCarlo Currie is a senior fellow at the Independent Women’s Forum.