Original Apartheid Hustler unveils the enigmatic life of Dugmore Boetie, a writer remembered for the posthumously published Familiarity is the Kingdom of the Lost (1969), his humorous autobiographical novel narrating the topsy-turvy life of a fictionalised Sophiatown-born youth from the 1920s to 1950s. Engaging multiple registers, Original Apartheid Hustler is a biographical study, an analysis of Boetie's writings, and a decolonial meditation on apartheid-era exploitation and erasure. Based on archival research and interviews with Boetie's family and friends today, the authors provide insight into Boetie's background, his struggle to find his place as an artist and writer, and his collaborations with prominent intellectuals, including Ruth First, Nat Nakasa, Nadine Gordimer, and Barney Simon. Simon, pivotal in globalising Boetie's work, controversially controlled his copyright, influencing his posthumous narrative. This book unravels webs of fact, fantasy, and myth, exposing the highly racialised socio-cultural, political, legal, and intellectual violence Boetie and his legacy suffered during and after apartheid. It reveals Boetie's resilient self-fashioning, his multiple fabricated identities, and the concealment of his disability and political activities. Original Apartheid Hustler is a profound contribution to debates about authorship, privilege, legacy, and race, from apartheid to the present day.