This paper presents an analysis of salesmen in Arthur Miller's play Death of a Salesman (1958), David Mamet's play Glengarry Glen Ross (1984), and in the movies The Pursuit of Happyness1 (2006) and The Wolf of Wall Street (2013), all of who were competing in a cruel world of trade and commerce with the aim of achieving the American Dream. The theoretical framework of the paper firstly discusses the political circumstances in England which consequently led to the creation of the American Dream in the New World. Furthermore, it analyzes its characteristics and shows that there were various versions of the American Dream throughout the history, depending on the political situation in the country, but also depending on the opinions and attitudes of people themselves. The main part of the paper analyzes the characters of the plays and the movies by discussing their ethics, language and communication, and attitude towards business and family, referring to Jim Cullen’s versions of the American Dream, in order to show that there are characters who succeeded in the rat race of the American Dream but that there are also those who got crushed under the pressure of it. In addition, the characters of the plays and the movies show a contrast when it comes to the characteristics of the American Dream because they were all written at a different time. Lastly, the paper reaches the conclusion by stating that the American Dream corroded over the years, meaning that the realization of the dream has completely changed. Nowadays, many people resort to crime and other illegal actions in order to actually achieve the dream and live a life worthy of their labor.