Masculine gender role conflict (MGRC) occurs when externally-imposed male gender role expectations have a negative impact on and consequences for men. The purpose of this study was to examine how men in a homogeneous setting (i.e., a college campus) compare on MGRC and psychological well-being, based on their self-identified sexual orientation. Utilizing canonical correlation analysis, 96 heterosexual men and 102 gay men were compared on four factors of MGRC (conflict between work and family, restrictive emotionality, restrictive affectionate behavior between men, and success, power, and competition) and five factors of psychological well-being (anger, anxiety, depression, self-esteem, and attitudes toward seeking psychological help). Findings for the heterosexual men were highly consistent with previous studies on MGRC and psychological well-being in a college-age population. Findings for the gay men indicated they had more problems with MGRC and psychological well-being than college-age and older gay men surveyed in the one published study on gay men and MGRC. Gay men who were single also reported more problems with restrictive emotionality, anger, anxiety, and depression, and had lower self-esteem, than gay men who were in a relationship. Between group differences were few, with gay men reporting significantly less restrictive affectionate behavior between men than heterosexual men. There were no significant differences between the two groups on any of the psychological well-being variables, indicating that the gay men were no more pathological than the heterosexual men with respect to their psychological well-being. Overall, the psychological well-being of both populations was seen to suffer as a result of increased MGRC. Implications are discussed for psychological interventions with men who are bound by traditional male gender role stereotypes.