In the present study we evaluated relationships among internalized stigma, subjective importance of masculine gender roles, and risky sexual attitudes and behaviors among men who reported same-sex attraction or behavior. A national U.S. sample of 95 men who identified as gay (79.4%), bisexual (10.3%), or another sexual orientation identity label (10.3%) participated via an online survey. Three mediation models examined the importance men placed on their own adherence to masculinity as a mediator of the relationships between internalized stigma and self-reported risky sexual attitudes and behaviors. The statistically significant direct relationships between internalized stigma and risky sexual behaviors (e.g., condomless sex, multiple partners) were negative, but the indirect effects through heightened importance of masculinity were positive. In contrast, both the direct and indirect effects between internalized stigma and sexually compulsive attitudes were positive. The results have implications for clinicians to specifically target internalized sexual stigma and attitudes toward masculine gender roles when working with sexual minority men at risk for high levels of risky sexual attitudes and behaviors. Implications for providing contextually grounded interventions (e.g., HIV prevention, sexual education) for sexual minority men are discussed.