Party like it’s 1925: Tobey Maguire and Leonardo DiCaprio star in the most recent version of The Great Gatsby, out in theaters in May. (Warner Brothers)
The story begins with a party at a Long Island estate, “a colossal affair by any standard … with a tower on one side, spanking new under a thin beard of raw ivy, and a marble swimming pool and more than forty acres of lawn and garden.” In its

blue gardens men and girls came and went like moths among the whisperings and the champagne and the stars.… On buffet tables, garnished with glistening hors d’oeuvre, spiced baked hams crowded against salads of harlequin designs and pastry pigs and turkeys bewitched to a dark gold…. The bar is in full swing and floating rounds of cocktails permeate the garden outside until the air is alive with chatter and laughter and casual innuendo and introductions forgotten on the spot.

It could be any estate and any party hosted by people whose wealth is recent and extravagant, for guests they may or may not know but who are irresistibly drawn into their aura. But in fact, or, rather, in fiction, it is a story of and about the 1920s. The estate is leased and the party hosted by Jay Gatsby, the central figure in F. Scott Fitzgerald’s much-loved 1925 novel, The Great Gatsby, now a Warner Brothers film directed by Baz Luhrmann and starring Leonardo DiCaprio.

What remains so compelling about Gatsby that investors have bet an estimated $127 million that this quintessential story about the 1920s will speak to audiences of today?

And not just today: Gatsby has been adapted for film five times in five decades, more than all Fitzgerald’s other novels put together. None of the decade’s other classics—The Sound and the Fury, The Sun Also Rises, The Age of Innocence, and All Quiet on the Western Front—have been made into films more than twice in the almost nine decades since they were written.

Gatsby’s enduring popularity may be attributable to the fact that while it was written in the 1920s about the 1920s, it tells a story that history has repeated over and over ever since. Just as it fits the boom and bust of the 1920s, it could also be about savings and loan executives in the 1970s, tech wizards and entrepreneurs in the 1990s, or purveyors of subprime mortgages and credit default swaps in the 2000s.

In fact, this latest film of the Fitzgerald masterpiece was conceived in 2008, as the world was reeling into the Great Recession, and with explicitly didactic intentions: “If you wanted to show a mirror to people that says, ‘You’ve been drunk on money,’ they’re not going to want to see it,” Luhrmann told the Hollywood Reporter when he acquired the rights to Gatsby. “But if you reflected that mirror on another time they’d be willing to.”

What has captivated us about Gatsby for so long?

The story’s narrator, Nick Carraway (played in the movie by Tobey Maguire), is fascinated by Jay Gatsby from the moment they meet at one of Gatsby’s sumptuous parties, where Carraway mistakes his host, a man in his early thirties, for another guest:

“I’m Gatsby,” he said suddenly.… He smiled understandingly—much more than understandingly. It was one of those rare smiles with a quality of eternal reassurance in it, that you may come across four or five times in life. It faced—or seemed to face—the whole external world for an instant, and then concentrated on you with an irresistible prejudice in your favor. It understood you just as far as you wanted to be understood, believed in you as you would like to believe in yourself and assured you that it had precisely the impression of you that, at your best, you hoped to convey. Precisely at that point it vanished.

Beyond the wealth that his estate and the lavishness of the party bespeak, Gatsby is shrouded in mystery, even to his guests. “Where is he from?” Carraway asks a companion. “And what does he do?… [Y]oung men didn’t—at least in my provincial inexperience I believed they didn’t—drift coolly out of nowhere and buy a palace on Long Island Sound.”

In time, of course, we learn that Gatsby’s wealth is both recent—made in the four years between the time he is mustered out of the Army after World War I and the summer of 1922, when the story takes place—and illegitimate, made in a relatively genteel sort of bootlegging in which liquor is sold through pop-up drugstores.

Gatsby’s decline and fall are as rapid as was his ascent. The dazzling parties end. “[T]he automobiles which turned expectantly into his drive stayed for just a minute and then drove sulkily away.” Before the summer ends, he is dead. His funeral is attended only by an erstwhile hanger-on, Carraway, and Gatsby’s father, “a solemn old man very helpless and dismayed.”

The rise and fall of Jay Gatsby parallels, of course, the story of the 1920s themselves: the rapid ascent, the fabulous unearned wealth, the smile of eternal reassurance that suddenly vanished, the abrupt and shocking crash, and the desolate end. And the book was written five years before the end—the stock market crash of 1929—took place.

But it also parallels the story of many of the decades since Gatsby. The scenarios have varied—from the over-leveraged stock market of the 1920s to the tech bubble of the 1990s to the recent subprime mortgage debacle. But at the center of them all is the lure of great wealth: not mere prosperity, but riches beyond the dreams of avarice, acquired suddenly, and almost as effortlessly, as finding a pot of gold at the end of a rainbow.

History tells us that the bubble of wealth acquired overnight is likely to deflate overnight when fantasy is punctured by reality. Sometimes, as with the tech bubble, the disappearance of wealth does little damage to the innocent. More often—the Great Depression, the S&L crisis, the subprime mess—it comes down the hardest on the least blameworthy and the most vulnerable with crushing consequences.

Yet, like that glum optimist Charlie Brown, who lets hope trump experience each autumn, we as investors cannot resist the wager, and we as spectators cannot resist watching them.

Perhaps that is part of the enduring appeal of The Great Gatsby. As many times as we have lived through the cycle of ill-gotten gains leading to catastrophic collapse—maybe the wages of sin really is death—the story never becomes stale or dated. It is hard for us to resist the smiles of eternal reassurance. We never tire of rising up and clustering around each successive Gatsby. We want to be them, or at least to be in their aura, to be the object of the kind of smiles that Jay Gatsby bestowed. And we never fail to be shocked when their smiles, their fortunes, and their auras vanish.

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Louis Barbash is a Washington writer who blogs at