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Contemporary views regarding masculinity have focused on the ways in which socialized masculine ideologies influence, particularly negatively, the physical and psychological lives of men. Although sport has been conceptualized as an environment in which hypermasculine ideologies (e.g., emphasis on competition and indifference to physical pain) are learned and reinforced, few studies have quantitatively explored how, or if, masculine norms and gender roles differ between athletes and nonathletes and may be related to psychological distress and help-seeking. Male collegiate athletes (n = 220) and nonathletes (n = 203) completed a series of questionnaires to assess their level of conformity to masculine norms and gender role conflicts, depression, substance use, self-stigma, and attitudes and intentions to seek help. Through a series of multivariate and mediational analyses, we found that (a) athletes reported significantly higher levels of masculine norms (e.g., heterosexual self-presentation) and role conflicts than nonathletes; (b) gender role conflicts, such as between work and family, significantly predicted depressive symptomatology, whereas masculine norms, such as risk-taking, were related to greater alcohol use; and (c) across both groups of men, self-stigma partially mediated the relationship of conformity to masculine norms to negative attitudes about, and intentions to seek, psychological help. Although athletes more strongly identified with certain masculine norms, in both groups of men, overall conformity to masculine norms, but not gender role conflict, predicted more negative attitudes about seeking help, both directly and through increases in self-stigma.