Using theories and concepts relating to the social construction of Black masculinity and male gender role conflict, the authors explored contextualized meanings of masculinities and corresponding behavioral expressions among 22 Black men enrolled at a private research university. The concepts of toughness, aggressiveness, material wealth, restrictive emotionality, and responsibility underscored the meanings the participants ascribed to masculinities. Participants expressed these concepts behaviorally through their pursuit of leadership and academic success, homophobia, and the fear of femininity, and through the sexist and constrained relationships they experienced with women. Based on the findings, practical implications for supporting the gender identity development and success of Black men during their undergraduate years are offered, as are recommendations for future research on the gender-related experiences of Black male undergraduates.