This dissertation advances an emerging critical interest in contemporary financial culture by both identifying a new genre, financial culture literature, and by theorizing its depictions of "80s businessmen" as iconic of late capitalism. I describe this genre's development in canonical and non-canonical works from the last three decades through sociological theories of risk (especially financial risk), and a history of Western economic practice. My dissertation first establishes financial culture literature's genealogy in modernist novels like Theodore Dreiser's The Financier (1912) and later in post-war novels like Richard Yates's Revolutionary Road (1961), texts that depict how business culture absorbs white-collar workers figures into paradoxically alienated, yet extreme social lives of starched-collar efficiency. Against this backdrop, I explain how the trade of new, massively lucrative credit "products" (derivatives, securities, junk bonds) made possible by Reaganomics' deregulation of banking practices created a new, bizarre class of risk-loving, fast-buck financiers, extreme in their disconnection from social responsibility and socioeconomic realities. Financial culture literature both critiques and glamorizes these figures; novels and films that represent the 80s businessman's glamorous world of penthouses and tinted windows with the extreme, shocking, or macabre, in order to unmask the businessman's heroic gambler's bravado as a form of corporatized violence and hedonism. Consequently, my dissertation reveals how fictional characters such as the film Wall Street's Gordon Gekko (1987) and American Psycho's Patrick Bateman (1991) are paradigmatic of an emerging literary tradition critical of (and fascinated by) the unsustainable life of new corporate worlds.