This chapter examines Kerouac in the context of 1950s literary culture in the United States, with particular emphasis on the Cold War. The 1950s was the decade Kerouac became famous overnight with the publication of On the Road, and the decade he produced the bulk of his most significant writing, including Visions of Cody, Doctor Sax, The Subterraneans, The Dharma Bums, and Mexico City Blues, among others. This chapter explores the relationship between Kerouac’s literary production during the 1950s and the multilayered cultural imperatives of the Cold War.