This dissertation examines the five biographies or memoirs written about the renowned South African writer Herman Charles Bosman. The main aim of the study is to show how different, and often contradictory, the views of him are as presented in the biographies. I also investigate different theories of biography as expounded by Leon Edel, Ira Bruce Nadel and Ray Monk and explore to what extent each of the biographies conforms, or does not conform to the theory. It is the contention of this dissertation that though the existing theories are useful and do shed light on each biographer’s approach and practice, they are also limited in accounting fully for the diverse and often discrepant accounts of Bosman’s life. The dissertation opens with an explication of several different theories regarding biography, and gives a brief overview of the life story of Herman Charles Bosman. Some of the main elements of biography (including different forms of narration, language and myth) are discussed and how they might be used in biography. The subsequent chapters focus on and offers detailed analyses of the biographies of Bosman, beginning with Herman Bosman As I Knew Him by Bernard Sachs and My Friend Herman Charles Bosman by Aegidius Jean Blignaut. Thereafter Sunflower to the Sun by Valerie Rosenberg and Life Sentence by Stephen Gray are analysed. Finally, there is an analysis of several reminiscences of those who knew Bosman, including Lionel Abrahams’s important memoir. The strengths and limitations of the various biographies are analysed, thereby shedding light not only on the practice of biography itself, but also on the complex and enigmatic figure of Herman Charles Bosman.