Considered to be one of the great American novels, F. Scott Fitzgerald’s The Great Gatsby tackles and dismantles the myth of the American Dream through its titular character Jay Gatsby, who reinvents himself in order to chase after his ambitions of achieving affluence and social status. Once having achieved that wealth, Gatsby succumbs to its influence without the benefits of its status due to him belonging in the class of so-called “new money.” This is mirrored in Patricia Highsmith’s The Talented Mr. Ripley as the young and money-hungry Tom Ripley manages to achieve both wealth and the “old money” status through more sinister means at the cost of his own identity. This thesis will further explore the relationship between wealth and how it forms a character’s identity as well as how the aspiration for wealth can be achieved in a post-World War I and post-World War II United States in order to showcase the disparity that had developed between classes in that time period. Furthermore, along with class identity, this thesis will also examine the way wealth transforms a character’s own identity and how it can shape gender identities within the novels. This will include how masculinity is defined within the male protagonists of The Great Gatsby and The Talented Mr. Ripley, as well as how femininity is interwoven with class in the female characters of The Great Gatsby. Moreover, this paper will also take a look into Nick Carraway as middle-man character; between old and new money ideal as well as between the masculine and feminine. Considering that both novels feature obsession as a main characteristic of want, this paper will delve further into the relationship money has with ambition and the obsessions of the two titular characters; Jay Gatsby’s desire for Daisy and her status, and Tom Ripley’s obsession with Dickie Greenleaf and his familial wealth. Moreover, this thesis will also survey the way wealth and its status are related to crime and the way differing classes face consequences.