This research positions F. Scott Fitzgerald’s The Great Gatsby as an insightful and truthful portrayal of the complexities of 1920s America, looking beneath the Jazz Age’s glittering exterior. The study shows how Fitzgerald’s novel skillfully blends historical events like the consequences of Prohibition, the distortion of the American Dream, and the clash between Old and New Money with enduring themes of unreachable love and faded dreams. By examining factors such as changing social values, the rise of the Flapper, and the influence of new technology, the research demonstrates that the novel captures the era’s ambitions and contradictions with striking clarity. All in all, Fitzgerald created a book that is both a cultural critique and a historical document, sharply exposing the materialism and inequality of the time. The Great Gatsby remains relevant because it explores the futility of recapturing the past and continues to spark conversations about what it means to live ethically in America.