Drawing from ethnographic, archival and secondary research, this article examines multiple-sexual partners in historical perspective in KwaZulu-Natal, a South Africa province where one in three people are thought to be HIV positive. Research on masculinities, multiple-partners, and AIDS has been predominantly directed towards the present day. This paper stresses the importance of unraveling the antecedents of contemporary masculinities particularly the gendered cultural politics through which they have been produced. Arguing against dominant conceptions of African masculinity as being innate or static, it charts the rise and fall of the isoka, the Zulu man with multiple-sexual partners, over the last century. Showing how the isoka developed through changing conditions occasioned by capitalism, migrant labour and Christianity, it contends that an important turning point took place from the 1970s when high unemployment threatened previous expressions of manliness, notably marriage, setting up an independent household and becoming umnumzana (a household head). The high value placed on men seeking multiple-partners increasingly filled the void left by men's inability to become men through previous means. Turning to the contemporary period, the article argues that, shaken by the huge AIDS deaths, men are betraying increasing doubts about the isoka masculinity.