Mailer’s philosophy of the Hipster is one of his most provocative: Outlined most clearly in “The White Negro,” “Reflections on Hip,” and “Hip, Hell, and the Navigator,” his figuration of the Hipster is an existentialist rebel, an “urban frontiersman” who lives in “the undercurrents and underworlds of American life” amongst “the defeated, the isolated, the violent, the tortured, and the warped.” Mailer’s characterization of the Hipster is the foundation for more than one of his later characters, and is reflective of his place on the periphery of countercultural groups like the Beats.

Mailer engages provocatively with themes of sexuality in a number of his novels, in a variety of ways – from the overt and somewhat shocking sex scenes in An American Dream to the exploration of sex and mysticism in Ancient Evenings to the subplot focusing in on closeted homosexuality in Harlot’s Ghost. Many of the theories of sexuality posited in these works are grounded in previous essays and nonfiction, and reflect not only the culture in which Mailer lived but provide insight into his ongoing attempt to represent sexuality in language. For example, the exploration of homosexuality in Ancient Evenings can be traced back to The Prisoner of Sex, where he was also interested in the way sex is used to enforce hierarchies of power within the prison system, and then back as early 1955, where, in “The Homosexual Villain,” Mailer was still working to flesh out “the edges of the rich theme of homosexuality,” struggling to find a place for it in his construction of contemporary masculinity.

Over the course of his career, Mailer demonstrated a deep concern regarding the problem of totalitarianism, particularly its manifestation in American society. It was his belief that totalitarianism was not only a political and social threat enacted against the freedom of the individual, but that it had also made inroads into every aspect of society, from architecture to technology. This chapter provides an overview of Mailer’s definitions of totalitarianism in society, as well as his views of its consequences – which he believed manifested not just socially and politically, but also psychologically and physically.