Men who have sex with men and women (MSMW) represent an important target population for understanding the spread of HIV because of the inherent bridging aspect of their sexual behavior. Despite their potential to spread HIV between gender groups, relatively little recent data have been reported about this population as a subgroup distinct from men who have sex with men only. This paper analyzes data from the Chicago site of Sexual Acquisition and Transmission of HIV Cooperative Agreement Program to characterize 343 MSMW in terms of their demographics, drug use, sexual risk behavior, sexual identity, and sex partners. Results show the MSMW sample to be extremely disadvantaged; to have high rates of drug use, including injection and crack use; to report more female than male sex partners; to not differ from gay and heterosexual men in rates of condom use; and, for the most part, to report sexual identities that are consistent with their sex behavior. MSMW represent an important subpopulation in the HIV epidemic and should be targeted for risk reduction interventions.