This article sets the itineracy of antiapartheid expressive culture to work in relation to exiled South African jazz singer Miriam Makeba. It revisits accounts of transnational cultural circulation on the part of Rob Nixon, Paul Gilroy, and others to argue that the diffusion of South African cultural formations outward from South Africa offers historiographic traction over other Cold War settings. Throughout the international antiapartheid struggle, South African expressive culture was channeled through local paradigms of reception in the world beyond, in taut negotiation with aesthetic, institutional, linguistic, and political considerations. Instances of cultural translation, catachresis, and slippage resulting from the deterritorialization of South African cultural formations can thus be contextualized, historicized, and turned back reflexively on other conjunctures, to defamiliarize existing scholarship. Makeba’s long exile in Ahmed Sékou Touré’s Guinea between 1969 and 1986 is examined in the light of these claims. Here, Makeba crosses a theater of intense ideological contestation following Touré’s 1968 socialist cultural revolution, illuminating some of its constitutive features. The article concludes with a consideration of Makeba’s agency as performer at the interface between militant cultural nationalism and state prohibition in revolutionary Guinea.