The Great Gatsby is 100 years old this year, which feels right in a way. After all those years as a perennial mainstay of the American high school English curriculum, all those Gatsby-themed flapper parties, all those valiant but ham-fisted attempts to adapt it, we know the beats of it well: the parties, the glamour, the green lights, and the beautiful clothes. It might as well be a hundred.

On the other hand, there are parts of Gatsby that feel so fresh and modern that they could have been written yesterday. In our own moment, as the world’s richest man takes a hatchet to the federal government for sport, one of Gatsby’s most celebrated lines about the very wealthy feels resoundingly true: “They were careless people … They smashed up things and creatures and then retreated back into their money or their vast carelessness, or whatever it was that kept them together, and let other people clean up the mess they had made.”

There’s something reassuring about knowing that Gatsby is the book we’ve chosen to put in classrooms and movie theaters, to make it one of those culture touchstones that everyone more or less knows at least a little.

But Gatsby did not become an immediate institution in American life, and we don’t know it as well as we think we do. Gatsby is a much more complicated book than its pop culture footprint suggests. It’s big enough to survive all those turgid high school essays about color symbolism and the American dream, all those drinking parties with girls in backwards headbands, all those mediocre movies and bad plays.

Here’s the story of how The Great Gatsby has endured — and why we keep misreading it.

How F. Scott Fitzgerald wrote a masterpiece and became a legend

As laid out by Matthew J. Bruccoli in the definitive Fitzgerald biography, Some Sort of Epic Grandeur, F. Scott Fitzgerald set out to fulfill his promise as one of the most promising novelists of his generation with The Great Gatsby in 1925.

His second book, 1922’s The Beautiful and Damned, had been considered a letdown. Readers agreed it was beautifully written, but felt nonetheless that it didn’t quite live up to the standard set in his acclaimed debut, This Side of Paradise. Critics began to wonder if Fitzgerald wasn’t a man “with a gift for expression without very many ideas to express.”

To write The Great Gatsby, Fitzgerald drew upon his own experience as the rejected poor suitor to multiple rich girls. He was from a middle-class family, but the fancy boarding school education that led him to Princeton had him rubbing elbows with the wealthy.

In college Fitzgerald dated a society debutante, whose father warned him that “poor boys shouldn’t think of marrying rich girls.” When he courted his eventual wife Zelda, also a debutante from money, he was an unemployed and unpublished writer. Zelda refused to marry him until he had a source of income, and Fitzgerald responded by building his own legend as a handsome, romantic, hard-living celebrity novelist, gallivanting from party to party across New York City.

These events provide the loose skeleton of the plot of The Great Gatsby: Poor young James Gatz falls in love with the glamorous socialite Daisy, but doesn’t have enough money to marry her. Gatz spends the next five years pursuing various illicit money-making schemes until he is as wealthy as an........

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