The notion of a certain identity crisis in capitalist culture, along with the tradition- ally critical portrayal of business in American film (Ribstein 2012), becomes par- ticularly manifest in cinematic narratives concerned with financial markets, stock trading, speculation, and the boundless possibilities of personal enrichment in such environments. The memorable Gordon Gekko (Michael Douglas) of Oliver Stone's Wall Street (1987) established the financial trader archetype, characterized by his charisma and magnetism, by the powerful driving force of greed and ambi- tion, and by his lack of ethical scruples in placing his self-interest above the social common good. Ever since, Hollywood brokers have tended to appear under the light of excessive masculinities and anti-social conducts, opposed to both their families and the economy, and they are often linked to criminal activities and hypersexualized hedonism (Brassett and Rethel, 2015, 443-445). The aim of this chapter is to explore, through film analysis focused on characters and dramatic devices, the ways in which the contemporary heirs of Wall Street develop and rein- force the dark undertones of this archetype. In order to do so, we will focus on Margin Call (J. C. Chandor, 2011), The Wolf of Wall Street (M. Scorsese, 2013), and The Big Short (A. McKay, 2015).