This article examines the ways literary adaptations between Hong Kong and Taiwanese writers shape literary cultures in both places during the Cold War period. The 1950s and 1960s were the time when Hong Kong and Taiwan literary cultures were starting to thrive. An influx of literati into both places collaborated with each other and the locals to experiment with literary forms in literary magazines. The 1950s and 1960s were also the time when Hong Kong and Taiwan cinema experienced the first waves of adapting literary works into film in the postwar period. After the literary magazine culture dwindled in the 1970s, a new generation of writers in both places emerged. In Hong Kong, these new writers may not be native, but they take Hong Kong as their main subject in their writings. The Taiwanese writer Shih Shu-ching is one of them. In studying Hong Kong-Taiwan literary adaptation histories, one may easily overlook the adaptation from fiction to screenplay, as in Shih and the Taiwanese playwright Wang Chi-mei's case. By understanding the literary relationship between Hong Kong and Taiwan in the Cold War, together with their adaptation histories, we can acquire a clearer sense of how these literary cultures developed.