This study tested the extent to which gender role attributes and gender role ideology account for sex differences in internally directed psychological distress and in externally directed deviant behavior in a random sample of 2,013 adolescents. Results indicate that gender roles substantially mediate sex differences in both types of pathology: Masculine instrumental attributes reduce internalized distress, whereas feminine expressive attributes reduce externalized behavior problems. In addition, conventional gender role attitudes were positively related to externalizing problems among male adolescents, but were unrelated to pathology among female adolescents. These associations were largely equivalent across Black and White racial groups and across age groups (13 to 19 years). Two alternative theoretical models linking gender roles and pathology are discussed.