This study uses an event-based approach to examine individual, relationship, and contextual correlates of heterosexual condom use among homeless men. Structured interviews were conducted with a predominantly African American sample of 305 men recruited from meal lines in the Skid Row area of Los Angeles. Men reported on their most recent heterosexual event involving vaginal or anal intercourse. Adjusting for demographic characteristics only, condom use was more likely when men had higher condom use self-efficacy, greater HIV knowledge, or talked to their partner about condoms prior to sex. Condom use was less likely when men held more negative attitudes towards condoms, the partner was considered to be a primary/serious partner, hard drug use preceded sex, or sex occurred in a public setting. Condom attitudes, self-efficacy, partner type, and communication were the strongest predictors of condom use in a multivariate model that included all of the above-mentioned factors. Associations of unprotected sex with hard drug use prior to sex and having sex in public settings could be accounted for by lower condom self-efficacy and/or less positive condom attitudes among men having sex under these conditions. Results suggest that it may be promising to adapt existing, evidence-based IMB interventions for delivery in non-traditional settings that are frequented by men experiencing homelessness to achieve HIV risk reduction and thus reduce a significant point of disparity for the largely African American population of homeless men.