As a response to significant changes in social conditions for minorities, the Miss Gay Western Cape (MGWC) annual pageant started in Cape Town almost immediately after the change in rights for homosexual and transgendered people that came with the establishment of the new South African constitution in 1996. Over the past two decades, the MGWC has become the most publicly visible and well-attended drag pageant in the Western Cape. In the article, I trace how the pageant – whose aim is to provide a platform for queers of color to perform in a secure environment without exploitation – entails a number of complex movements: across the urban landscape, between poorer peripheral suburbs (Cape Flats, Atlantis) and the predominantly white city center; among and between gender identities, from a fluid and performative conception of drag to the intentional fixity of trans identities; from local performance contexts to the powerful influence of the global phenomenon RuPaul’s Drag Race, a US reality television program in which performers compete for the title “America’s next drag superstar.”