The HIV/AIDS epidemic in South Africa has largely focused on the needs of heterosexual men and women. However, little is known about the sexual risk histories of men who have sex with both men and women (MSMW). Furthermore, we know very little about the psychosocial health needs or of the possibility of a syndemic (numerous interrelated epidemics) among MSMW. We surveyed 1,203 men attending drinking establishments in a township located in Cape Town, South Africa. We compared the behaviors and experiences of MSMW to men reporting only having sex with women (MSW). Twelve percent of the sample reported having sex with both men and women in the past 4 months. MSMW were twice as likely as MSW to report being HIV positive (10.5 vs. 4.6 %). MSW were more likely to be married than MSMW but reported similar numbers of female sex partners. MSMW were more likely to report a history of childhood sexual abuse, recent experienced and perpetrated physical and sexual partner violence, both receiving and giving sex for money, drugs, or shelter, and a recent STI. These factors were found to be interrelated among MSW but not MSMW. Although MSMW demonstrate considerable risk taking and report higher rates of HIV infection than MSW, their needs are largely unmet and underemphasized. Findings suggest the need to better understand factors contributing to sexual risk taking among MSMW. HIV prevention interventions should consider psychosocial health problems unique to MSMW residing in South African townships.