This chapter explores the politicisation of literature during the period of the Cold War. It argues that literature became a key coin in the cultural cold war, invested with the power to represent working-class subjectivity and class struggle by the Soviets, and construed as embodying and igniting individual liberty by the US. Literary writers and literature, during the cultural cold war, were both censored and funded as never before. While the Soviets took control of book production by both censoring and funding writers, the US pumped enormous sums of money into funding global literature deemed representative of individual freedoms. The literary dissident, stifled by the East and lionised by the West, was a key figure in cultural cold war politics. The chapter focuses on two very different kinds of writers, Stephen Spender and Doris Lessing, who were shaped by the conditions of the cultural cold war. Both writers viewed their literary writing in the light of the politics of the Cold War, and used their writing to explore the political issues of censorship, freedom, and dissidence.