During the Cold War, socialist countries in the Eastern Bloc forged fraternal relations with newly independent states on the African continent and other parts of the Third World. These alliances translated into economic exchanges, political and ideological ties, and cultural solidarities. Oftentimes subsumed under the rubric of internationalism, these understudied cultural exchanges reflect both the forward thinking elements of global socialism as well as the paternalist and condescending aspects of relations between the Second and the Third Worlds. In order to analyze the legacies of these solidarities in the twenty-first century, the author looks at the work of Wanlov the Kubolor, which is the stage name of Emmanuel Owusu-Bonsu, a Ghanaian-Romanian musician, poet, film director, and activist. Describing himself as an “African Gypsy” and a peripatetic trickster (a “kubolor”), Wanlov draws on Ghanaian and Romanian artistic traditions to forge a unique perspective on postsocialist societies, from the margins of the capitalist world-system. The work of artists such as Wanlov the Kubolor presents a clear-eyed East/South perspective on global phenomena: consumerism, the quick cooptation and taming of oppositional aesthetics into commercial art, racism, and class distinctions, yet also possible new directions for activism and resistance.