My project examines how signifiers of working-class coloured or "mixed race" South African identity have been variously deployed via Cape Town-based hip-hop, both during and after the end of formal apartheid. Inspired by the 1976 Soweto Uprising and coming of age in the late 1980s, working-class coloured youth drew easy parallels between the insurgent narratives of "Golden Age" US hip-hop, and their own lived experiences. By rapping in "Kaaprikaans," a vernacular form of Afrikaans endemic to the Cape Flats (an area of the city reserved for "coloured development"), this musical genre became synonymous with the expression of coloured cultural identity. Early Cape Town hip-hop advocated resistance to apartheid: musicians rejected the term "coloured" in favor of an "African" or "Black Consciousness" identification. Whereas the apartheid regime reduced individual identity to phenotypical racial classification, nineties "Rainbow Nationalism" heralded new opportunities for the expression of ethno-racial identity. Recently, white, middle-class Cape Town rappers have been adopting working-class coloured language and cultural markers, reaping considerable social and financial benefits in local and especially global markets. My research asks: How are marginalized coloured hip-hop artists, those progenitors of the style still active today, responding? How are attempts at coloured self-representation via hip-hop being affected? I propose that in order to reclaim these ethno-racial articulations, "old-school" musicians are reverting to fixed conceptions of "colouredness." This move constitutes a pragmatic, or strategic essentialism on the part of coloured artists. How then is the interplay between an expansive "black" and a truncated "coloured" identity ultimately reconciled?