Due to the heterosexist ideals associated with gender norms, gay men often experience negative attitudes towards their own sexuality—internalized homophobia. As a result, gay men often feel compelled to compensate for their perceived lack of masculinity. The study aimed to investigate the relationship and predictive power of masculinity on gay men’s experiences of internalized homophobia. A sample of 489 self-identified Australian gay men 18–72 years old participated in an online survey on masculinity and homosexuality. Descriptive statistics, bivariate correlations, and sequential multiple regressions were used to test the study’s aims. Sequential multiple regressions revealed that conformity to masculine norms and threats to masculinity contingency were stronger predictors of internalized homophobia over and above demographic and other factors. Given the already known psychological risks associated with social isolation, internalized homophobia, and the poor mental health outcomes associated with sexual minority groups, it is suggested that gay men who are experiencing high degrees of internalized homophobia should not be distancing themselves from other gay men but, conversely, seek a strong relationship with the LGBTI community.