The current assessment was undertaken to examine the link between drug use and sexual risk behavior among men who have sex with men (MSM) in locations known to have high prevalence rates of drug use and sexual risk behavior in Cape Town, Durban and Pretoria, South Africa. Street intercepts and purposive snowball sampling were used to recruit drug-using MSM. A rapid assessment was undertaken which included observation, mapping, key informant interviews and focus group interviews with MSM. Drug using key informants were tested for HIV. The use of drugs like crack cocaine, cannabis and methamphetamine to specifically facilitate sexual encounters was evident. Drugs led to inconsistent condom use and other high-risk sexual activities despite HIV risk knowledge being high. Many injecting drug-using MSM shared needles and reused equipment. Among MSM who agreed to HIV testing, one-third tested positive. Views about drug and HIV treatment and preventive services and their efficacy were mixed. Various barriers to accessing services were highlighted including homosexual stigmatization and availability of drugs in treatment facilities. Recommendations include addressing the gap between HIV-risk knowledge and practice, extending VCT services for MSM, increasing the visibility of drug abuse services within communities, addressing concerns about drug availability in treatment centers as well as reintegration issues and the need for after-care services, reducing stigmatization in drug and HIV services for MSM and finally, strengthening the link between drug treatment services and HIV prevention by integrating HIV/drug-related risks into HIV prevention efforts and HIV risks into drug use prevention efforts.