This essay makes the first sustained study of the Okinawan artist Makishi Tsutomu (1941–2015) who used American Pop Art vocabularies to describe the complex realities of US-occupied Okinawa. Focusing on his 1972 installation Commemorating the Reversion to the Great Empire of Japan, the essay examines the critical ambivalence of Makishi's Political Pop as a translation strategy. Despite his critique of both American and Japanese imperialism, Makishi was aware that Okinawa was inseparably entangled in it, especially in the context of the Vietnam War, which brought violence, but also economic benefits, to Okinawa. Despite his use of the American Pop idiom as a new lingua franca for contemporary art, Makishi's work did not reach either mainland or international audiences as the artist exhibited almost exclusively in Okinawa. By comparing Makishi's artistic strategies with those of a representative Okinawan novelist, Ōshiro Tatsuhiro, especially as articulated in his 1967 novella The Cocktail Party, the essay situates the significance of Makishi's project within the emerging discourse on the global neo-avant-garde.