This article brings together two distinct forms of engagement with Shakespeare by Black South and southern African writer-intellectuals in the 1950s and 1960s. Writers associated with Drum magazine and Sophiatown quoted from and adapted Shakespeare in their performance of a cosmopolitan identity resisting the strictures of the early apartheid period. At the same time, there was a modest boom in translations of Shakespeare into African languages. With the exception of K.E. Masinga, who translated and adapted nine plays as serialised radio dramas, the translators of this era—who worked as teachers or in the education system—produced texts that were primarily intended for use in schools. The intersection of this phenomenon with Bantu Education policies and practices complicates the story of South African Shakespeare translations. The Drum writers and the translators have previously been confined to separate areas of enquiry; here, we place them alongside one another, aiming to generate new insights into their shared historical moment by studying their differences but also by identifying commonalities.