Focusing on the major writings of James Baldwin and Norman Mailer, this chapter argues that the interpretative horizon of their works is inextricable from the emergence of modern conservatism as a cultural and electoral force. Whereas movement conservatives in the 1950s tended to stress tradition-based hierarchies and organic social order over abstract theories of individual liberty, conservatives began to shift their emphasis in the mid-sixties toward the language of unadulterated patriotism, property rights, and colorblind individualism. In this next stage of their movement, conservatives embraced an ideologically rigid fusion of laissez-faire capitalism and cultural populism that would redirect perceptions of literary value and prestige within American conservatism toward certain conservative strands of New Journalism and, in later years, toward the one-dimensionality of mass-market genre fiction. Finally, conservatives emphasized the “liberal cultural elite” trope with renewed vigor, constructing a monolithic stereotype of white liberal intellectuals whose racial guilt fueled their appetite for difficult, morally complex literature, a form of moral masochism that conveniently helped those same white liberals accrue “hip” cultural capital.