Black men who have sex with men (MSM) contract HIV at disproportionately high rates, and National HIV/AIDS Strategy goals to reduce HIV incidence cannot be successful without improved HIV prevention among racial minority MSM. A total of 210 Black MSM from three cities (Cleveland, Miami, and Milwaukee) completed measures assessing their sexual behavior and demographic characteristics, as well as AIDS-specific psychosocial scales, broader contextual domains, and substance use. Nearly 50% of men reported recent unprotected anal intercourse (UAI), often with non-main partners, with partners not known to be HIV seroconcordant, or with multiple partners. Thirty-seven percent of men reported being HIV positive. In multiple regression analyses, higher levels of unprotected behavior were predicted by weaker perceived peer norms for condom use, weaker risk reduction behavioral intentions, being HIV negative, and recent use of marijuana, cocaine/crack, and poppers. Greater number of UAI partners was associated with weaker perceived peer condom use norms, lower risk reduction intentions, illicit use of prescribed opiates, and fewer AIDS conspiracy beliefs. These findings suggest important factors that should be targeted in HIV prevention programs for Black MSM.