Set on the prosperous Long Island of 1922, The Great Gatsby provides a critical social history of America during the Roaring Twenties within its fictional narrative. That era, known for widespread economic prosperity, the development of jazz music, flapper culture, new technologies in communication (motion pictures, broadcast radio, recorded music) forging a genuine mass culture, and bootlegging, along with other criminal activity, is plausibly depicted in Fitzgerald's novel. Fitzgerald uses many of these societal developments of the 1920s to build Gatsby's stories, from many of the simple details like automobiles to broader themes like Fitzgerald's discreet allusions to the organized crime culture which was the source of Gatsby's fortune. Fitzgerald depicts the garish society of the Roaring Twenties by placing the book's plotline within the historical context of the era.
Fitzgerald's visits to Long Island's North Shore and his experience attending parties at mansions inspired The Great Gatsby's setting. Today, there are a number of theories as to which mansion was the inspiration for the book. One possibility is Land's End, a notable Gold Coast Mansion where Fitzgerald may have attended a party. Many of the events in Fitzgerald's early life are reflected throughout The Great Gatsby. Fitzgerald was a young man from Minnesota, and, like Nick, who went to Yale, he was educated at an Ivy League school, Princeton. Fitzgerald is also similar to Jay Gatsby in that he fell in love while stationed far from home in the military and fell into a life of decadence trying to prove himself to the girl he loved. Fitzgerald became a second lieutenant and was stationed at Camp Sheridan in Montgomery, Alabama. There he met and fell in love with a wild 17-year-old beauty named Zelda Sayre. Zelda finally agreed to marry him, but her preference for wealth, fun, and leisure led her to delay their wedding until he could prove a success. Like Nick in The Great Gatsby, Fitzgerald found this new lifestyle seductive and exciting, and, like Gatsby, he had always idolized the very rich. In many ways, The Great Gatsby represents Fitzgerald's attempt to confront his conflicted feelings about the Jazz Age. Like Gatsby, Fitzgerald was driven by his love for a woman who symbolized everything he wanted, even as she led him toward everything he despised.
In her book Careless People: Murder, Mayhem and the Invention of The Great Gatsby (2013), Sarah Churchwell speculates that parts of the ending of The Great Gatsby were based on the Hall-Mills Case. Based on her forensic search for clues, she asserts that the two victims in the Hall-Mills murder case inspired the characters who were murdered in The Great Gatsby.