According to theories of sexuality and gender advanced by Judith Butler, one’s gender is in constant flux throughout the course of a lifetime (Butler 1993).1 In their recent work, South African artists Paul Emmanuel (b. 1969) and Diane Victor (b. 1964) explore the vicissitudes of gender for (predominantly) white South Africans as this population is caught in the maelstrom of changing social forces. Both artists use portraiture to personify the individual in a state of extreme vulnerability, as the categories gender and racial identity, and their established hierarchies, are in flux. Both offer highly tactile engagement with the physical bodies represented while inventing visual means to dissolve the solidity of the flesh, presenting it as in passing from one state into another. Both use labor-intensive processes both to fix a moment and to suggest the transitory nature of human life. In Emmanuel’s digital video 3SAI: A RITE OF PASSAGE (2008; part of the installation project Transitions), and Victor’s Transcend and Lost Words series (2009, 2010), identity is unstable and gender indeterminate, potentially subject to irretrievable loss. Each series is a requiem, an invocation to meditation and mourning, but ultimately as well a path to transcendence via the shedding of embodied stereotypes. This paper will explore how each artist addresses gender concerns within specific South African contexts. Within the field of gender studies broadly, a split still exists in academic writing between masculinity studies and women’s studies. Bringing together Emmanuel’s work, which deals almost exclusively with issues of masculine identity, with Victor’s, which explodes conventional ideas of both femininity and masculinity in the context of a patriarchal culture, provides an opportunity to help bridge that gap. If Emmanuel’s work aligns closely with current theories of masculinity, Victor could be considered an outlier in terms of the parameters of feminist discourse, as she offers both male and female equal opprobrium; neither gender is considered morally superior or suffering from greater oppression. However, as white artists highly attuned to the legacies of the apartheid era, both artists link gender and racial identities to highly vulnerable situations—the military or the aging, infirm body—and in so doing test cultural norms of gender. In the works under discussion (the major series by both artists from 2008–11), Emmanuel has depicted males exclusively and Victor males predominantly, suggesting that for both artists masculinity is an especially pressing topic in South African culture today. The differences between their work are telling, however. Emmanuel’s work is oblique and poetic, whereas Victor’s is stark and confrontational; one might argue that their very aesthetics deny gender stereotypes.