Gender role conflict may influence condom use among black MSM. We examined relationships between the Gender Role Conflict Scale (GRCS), social/demographic variables and condom use among 456 black MSM. Higher total GRCS scores did not predict unprotected insertive anal intercourse (UIAI) or unprotected receptive anal intercourse (URAI) with men, but were associated with unprotected vaginal or anal intercourse (UVI/UAI) with women among bisexually active participants (n = 69). Higher perceived HIV risk reduced the likelihood of both UIAI and URAI with men. Internet recruitment venues, sexual discrimination experiences, higher numbers of sex partners and UVI/UAI with women all increased the likelihood of UIAI with men, while education (college/technical school or college degree) was associated with URAI with men. Future sexual health interventions for black MSM should emphasize broader social/demographic and alternative gender role variables with male sexual partners, while traditional GRCS variables may prove useful among those with female sexual partners.