This chapter traces the history of masculinity in South Africa, particularly in Cape Town. It shows that in the past, manhood was partly defined through vulnerability, because a man was made through allowing the influence of family, community, and metaphysical forces in Christianity, Islam, and indigenous African cosmologies. I argue that the term ‘patriarchy’ limits a nuanced understanding of gender in history. I call for a distinction between hierarchies based on ontological difference and ontological egalitarianism in gender studies. In South Africa’s history, men had to serve social collectives based on race, class, ethnicity, and religion. However, the value of being affected by others in hierarchical social orders was gradually superseded by the ideal of individual freedom. In the wake of colonialism, apartheid, and liberal democracy in turn, assemblages of masculinity increasingly fostered notions of individualism and self-reliance, first for British settlers, then for Afrikaners and Colored people, and finally for Black Africans. The development of Cape Town as a ‘modern city’ ultimately came not only with more gender equality, but also with a neoliberal market economy and gendered commodity consumption, at the expense of affective health in relationships.