Coloured South Africans have long been marginalized by a Black/White racial binary that framed their identities and cultural practices as degraded and derivative. Situated in a postapartheid twenty-first-century global neoliberal “identity economy” in which they continue to labor for cultural recognition and value, this article argues that contemporary practitioners of Kaapse klopse (clubs of the Cape) craft aesthetics beyond that binary that recenter musicking and musical value around community tradition and the feelings produced through iterative listening. I focus on the “sentimental” song category (English-language popular love songs) to show how performers and their audiences use sentimentals to orient themselves as racialized subjects and in the process frame popular musicking as a dynamic social experience rather than a matter of cultural (or racial) authenticity.