Numerous studies have documented gender differences in psychopathology; girls generally report more internalizing symptoms and boys generally report more externalizing symptoms. These gender differences are partially accounted for by the gender-typed personality characteristics of boys and girls. This study was designed to investigate how gender roles influence symptoms of psychopathology by examining the mediating effects of self- and peer-rated competencies. Using a multiple regression approach to path analysis with a sample of primarily White, middle-class high school students, gender roles significantly predicted symptoms of psychopathology and mediated the gender differences in those symptoms. In addition, the adolescents' self- and peer-rated competence in various domains helped to explain the effect of gender roles on symptoms of psychopathology. Specifically, self-rated social attractiveness and global self-worth fully mediated the relation between instrumentality (i.e., masculinity) and internalizing symptoms. Global self-worth and both self- and peer-rated achievement/conduct partially mediated the relation between expressivity (i.e., femininity) and externalizing symptoms. Practical and theoretical implications are discussed.