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.