"The Great Gatsby", the iconic novel of Fitzgerald is used as a guide to unravel the most significant aspects of the Roaring Twenties. This unique period of unprecedented economic growth is best described in the nine chapters of "The Great Gatsby", in which one can clearly understand the impact of WWI on the U.S society. The Prohibition era with bootleggers and speakeasies along with the "flappers" are highlighted in this paper. The notions of "class" and "race" are underscored in "The Great Gatsby" along with Jazz music, Automobiles and the American Dream. Last but not least, the thesis refers to the cinematic representation of the Roaring Twenties in the various Gatsby movies.