Thinking and writing about Caribbean aesthetics—as such—has become increasingly respected in the academy and in institutional art world spaces. However, the history of the influence of Caribbean thought and aesthetics is long and often uncredited or sublimated in other scholarly and artistic conversations. Roundtable speakers share how they are thinking about Caribbean aesthetics in relation to the question of the avant-garde, the limit, the edge, or the horizon of creative thought. Questions include: Is it useful to think about Caribbean aesthetics as “edgy”? What is the edge between a Caribbean aesthetic and a Caribbean politics? How do Caribbean aesthetics—including literature, the visual and plastic arts, performance, and music— explore, engage with, or efface the region’s violent histories of colonialism and enslavement? How do Caribbean aesthetics explore, engage with, or support nationalist and even authoritarian discourses?