More than any other author, F. Scott Fitzgerald can be said to have captured the rollicking, tumultuous decade known as the Roaring Twenties, from its wild parties, dancing and illegal drinking to its post-war prosperity and its new freedoms for women.

Above all, Fitzgerald’s 1925 novel The Great Gatsby has been hailed as the quintessential portrait of Jazz Age America, inspiring Hollywood adaptations populated by dashing bootleggers and glamorous flappers in short, fringed dresses.

But amid that decade of newfound prosperity and economic growth, Fitzgerald—like other writers of the so-called “Lost Generation”—wondered if America had lost its moral compass in the rush to embrace post-war materialism and consumer culture. While The Great Gatsby captures the exuberance of the 1920s, it’s ultimately a portrayal of the darker side of the era, and a pointed criticism of the corruption and immorality lurking beneath the glitz and glamour.

World War I echoes in the 1920s.

Set in 1922, four years after the end of the Great War, as it was then known, Fitzgerald’s novel reflects the ways in which that conflict had transformed American society. The war left Europe devastated and marked the emergence of the United States as the preeminent power in the world. From 1920 to 1929, America enjoyed an economic boom, with a steady rise in income levels, business growth, construction and trading on the stock market.

In The Great Gatsby, both Nick Carraway, the narrator, and Jay Gatsby himself are veterans of World War I, and it is Gatsby’s war service that kicks off his rise from a “Mr. Nobody from Nowhere” (in the words of his romantic rival, Tom Buchanan) to the fabulously wealthy owner of a mansion on West Egg, Long Island.

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The Marlborough House, a speakeasy haven for drinking socialites during prohibition.

Speakeasies flourished when Prohibition failed.

Beginning in early 1920, the U.S. government began enforcing the 18th Amendment, which banned the sale and manufacture of “intoxicating liquors.” But banning alcohol didn’t stop people from drinking; instead, speakeasies and other illegal drinking establishments flourished, and people like the Fitzgeralds made “bathtub gin” to fuel their liquor-soaked parties.

“The whole plot [of The Great Gatsby] is really driven by Prohibition in an important way,” says Sarah Churchwell, professor of humanities at the University of London’s School of Advanced Study and author of Careless People: Murder, Mayhem and the Invention of The Great Gatsby (2014). “The only way in which Jay Gatsby becomes wealthy overnight is because Prohibition created a black market,” allowing bootleggers like Gatsby and his partners to amass staggering quantities of money in a short time.

Prohibition creates a ‘new money’ class.

As their wealth grew, many Americans of the 1920s broke down the traditional barriers of society. This, in turn, provoked anxiety among upper-class plutocrats (represented in the novel by Tom Buchanan). In The Great Gatsby, Prohibition finances Gatsby’s rise to a new social status, where he can court his lost love, Daisy Buchanan, whose voice (as Gatsby famously tells Nick in the novel) is “full of money.”

“One of the many unintended consequences of Prohibition was that it created this accelerated upward social mobility,” Churchwell explains. “Fitzgerald is reflecting a preoccupation at the time that there were these upstart—as they would have said—these nouveau riche people who came from dubious backgrounds and then suddenly had all this money that they were splashing around.”

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A 1925 flapper.

The flapper was emerging.

By 1925, when Fitzgerald published The Great Gatsby, flappers were out in full force, complete with bobbed hair, shorter skirts and cigarettes dangling from their mouths as they danced the Charleston. But while later Hollywood versions of Gatsby channeled flapper style, the novel itself actually captures a comparatively conservative moment, as 1922 could be considered closer to 1918 than to the heyday of the Roaring Twenties later in the decade. For one thing, the Charleston didn’t even emerge until 1923. Also, Churchwell says, “skirts in the novel are a lot longer than we think they are. We all picture them in knee-length dresses. But dresses in 1922 were ankle-length.”

Jordan Baker, the novel’s most liberated female character, pushes against some of the restrictions still constraining women by the early ‘20s: She’s athletic, single and goes out with various men. “But her society is by no means welcoming that with open arms, and she's getting pushback,” Churchwell says, noting that Tom and Daisy Buchanan, as well as Jordan’s aunt, all voice disapproval of her behavior. “As with Gatsby, and his dark path to upward social mobility, the novel is charting a cultural moment that was anxious about women's new emancipation as much as it was celebrating it.”

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American professional gambler Arnold Rothstein, who inspired the Gatsby character Meyer Wolfsheim.

The novel depicts decay beneath decadence.

Just as Gatsby’s shifty business partner, Meyer Wolfsheim, was based on the real-life New York gangster Arnold Rothstein, widely believe to have fixed the 1919 World Series, the growing crime and corruption of the Prohibition era is strongly reflected in The Great Gatsby. In Churchwell’s book, she resurrects a real-life crime that made headlines in 1922—the double murder of an adulterous couple in New Jersey—and uses it to explore the background against which Fitzgerald composed his famous novel.

“It typifies a certain kind of story about the dark underbelly of the Jazz Age that is very present in [The Great Gatsby],” she says of the murder of Rev. Edward Hall, a pastor, and Eleanor Mills, a singer in his church’s choir. “It's about adultery, it's about people who make up romantic pasts, and it's about the sordidness of it all, the tawdriness of it all and the kind of dark griminess of it.”

New consumer culture leads to a rise in advertising.

Though not all Americans were rich, many more people than before had money to spend. And there were more and more consumer goods to spend it on, from automobiles to radios to cosmetics to household appliances like vacuums and washing machines. With the arrival of new goods and technologies came a new consumer culture driven by marketing and advertising, which Fitzgerald took care to include, and implicitly criticize, in The Great Gatsby.

“There’s this idea that America is worshipping businesses, it's worshipping advertising,” Churchwell says. In one memorable example, the cuckolded George Wilson believes the eyes of Dr. T.J. Eckleburg, a figure that appears on a giant billboard above the road, are those of God.

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Women in fur coats standing by a luxurious convertible, circa 1920.

The age of the automobile is reflected in Gatsby’s downfall.

Cars had been invented early in the 20th century, but they became ubiquitous in the 1920s, as lower prices and the advent of consumer credit enabled more and more Americans to buy their own. The liberating (and destructive) potential of the automobile is clear in The Great Gatsby, as Gatsby’s flashy, expensive car becomes the source of his downfall.

The novel predicts doom ahead.

Gatsby’s dreams of winning Daisy for himself end in failure, just as America’s era of prosperity would come to a screeching halt with the stock market crash of 1929 and the onset of the Great Depression. By 1930, 4 million Americans were unemployed; that number would reach 15 million by 1933, the Depression’s lowest point.

By 1924, when Fitzgerald wrote The Great Gatsby, he seems to have already foreseen the lasting consequences of America’s heady romance with capitalism and materialism. Through his novel, Fitzgerald foreshadows the inevitability that the decadence of the 1920s—what he would later call “the most expensive orgy in history” would end in disappointment and disillusionment.

“This novel is really a snapshot of a moment when in Fitzgerald's view, America had hit a point of no return,” Churchwell says. “It was losing its ideals rapidly, and he's capturing the moment when America was turning towards the country that we've inherited.”