Classical reception studies have developed into a vibrant field of research. Over the last decade, a new paradigm has evolved that studies often conflicting and heterogeneous receptions of classical literature in African American and Caribbean contexts. What is now commonly referred to as “black classicism” is, against this background, both a socio-political phenomenon and a cultural theory. In my essay, I want to focus on one author who has commented on “black classicism” in a theoretical as well as poetical way: Reginald Shepherd’s writings repeatedly draw on the classical canon, re-situating it in an African American context and re-reading its contents from the perspective of an outsider in order to undermine racial essentialisms. However, they do not function exclusively as counterdiscourses, but can rather be seen as an imaginative framework for thinking about the cultural fabrics of classicisms and the liberating potential they entail. This essay, then, discusses the cultural-historical and theoretical implications of Shepherd’s work against a review of his variant of “black classicism” before moving on to explore the transnational and transcultural imagination it inspires.