Research on men's gender roles over the last twenty-seven years has found a significant relationship between gender role conflict and psychological distress. Furthermore, this body of research has explored between group differences, in which racial identity was found to have mediating effects on gender role conflict and psychological distress. Nevertheless, research exploring African American male group differences, in terms of these three variables, are non-existent. The purpose of this investigation is to examine the extent to which racial identity statuses mediate the relationship between gender role conflict and psychological distress among Black college and formerly incarcerated men. Accordingly, these variables were explored using a sample of 81 participants consisting of Black college male and formerly incarcerated Black male participants. In general, findings from this study indicates that there are small differences between men that have served time and college males on masculinity, racial identity, and psychological distress variables.