This article offers a snapshot of South African hip hop by focusing largely on the uptake of ‘conscious’ hip hop in the 1980s and 1990s. It argues that especially Cape Town activists made meaningful contributions to advancing Black multilingual expression and, thereby, validating negated Black identities as the country was beginning to make the transition from apartheid to a democratic, post-apartheid South Africa. Ultimately, it questions whether the binary opposition between ‘conscious’ and commercial hip hop or Cape Town vs. Joburg hip hop is helpful in understanding the nuances of South African hip hop by pointing to examples that complicate such binaries.