This study examined longitudinal relations among adolescents' family relationships, peer relationships, and problem behavior. Participants were 1,357 African American and European American adolescents who were interviewed at 3 time points: 7th grade (mean age = 12.7 years), the summer after 8th grade (mean age = 14.2 years), and 11th grade (mean age = 17.1 years). For all racial and gender groups, 7th-grade family characteristics (youth perceptions of autonomy and warmth) predicted a risky peer context during 8th grade, which in turn predicted problem behavior during 11th grade. Additionally, problem behavior in the 7th grade predicted 11th-grade problem behavior, directly as well as indirectly through the peer context. Racial and gender differences are discussed, as are implications for future research.