In this essay, a productive critical dialogue is established between Philip Roth’s and John Updike’s representations of Prague under communism in The Prague Orgy (1985) and “Bech in Czech” (1987). Focusing on two central threads in both works: the intertwining of literature and politics, and Prague as a Jewish city, this essay argues that in mapping Prague, Roth and Updike revisit their protagonists’ emblematic concerns, as well as reflect on the role of the writer and literature under different political systems, questioning George Steiner’s conception of literature in the process.