The advent of the popular culture phenomenon allowed the definition and therefore the confinement and treatment of madmen, in the literary sense, to change, evolving into a complicated interaction within the cultural structures introduced by Foucault in Madness and Civilization. In his work, Foucault promotes the triptych of society at large, a mediator, and the madman, wherein society creates the mediator, usually the doctor or asylum, in order to come to terms with madness. At the end of the 20th century, however, postmodernism’s interaction with popular culture blurred this triptych. This suggests that in the latter half of the twentieth century the recognition of the culture industry as an important cultural phenomenon also changed the way in which society reacts to, defines, and deals with madness and the madman. In the postmodern age, the madman retains many of the stigmas he received during the Enlightenment. Yet, he is also a product of the culture industry, an entity who defines his world by mass-market strictures and standards. Like the rest of the postmodern world, the postmodern madman lives and dies by his relationship to popular culture illusions. I therefore argue that postmodern madness is the confusion created when the euphoria of living in a mass-produced fantasy world clashes with the need to retain one’s individual nature within such a realm. In this environment, the postmodern madman becomes the source of any mediators that may be placed between society and madness. The mediator, in this case, is a result of the individual’s need to conform, not to society’s rules, but to society’s illusions. The novels analyzed in this dissertation, Carlos Fuentes’s Zona sagrada [Holy Place], Walker Percy’s The Moviegoer, Manuel Puig’s El beso de la mujer araña [Kiss of the Spider Woman], Kurt Vonnegut’s Breakfast of Champions, Caio Fernando Abreu’s Onde andará Dulce Veiga? [Whatever Happened to Dulce Veiga?], and Bret Easton Ellis’s American Psycho present nuanced readings of the postmodern condition and its propensity toward madness, suggesting an evolutionary progression of Foucault’s structures which continuously alters the form of the mediator.