This study investigated associations between peer status, peer group social influences, and risk-taking behaviors in an urban sample of 647 African American seventh-grade students. The highest rates of problem behaviors were seen in the controversial peer status group, or those youth who were both highly liked and highly disliked by other youth. Findings also revealed contrasting patterns of peer group leadership. The more conventional, positive leadership style predicted lower rates, and the less mainstream, unconventional style predicted higher rates of involvement in problem behaviors. Conventional leaders were most likely to be popular status youth, while unconventional leaders were mostly to be both controversial and popular status youth. Controversial status youth were also more likely to be involved in deviant peer groups. Results highlight the importance of controversial status students as key influence agents during early adolescence. We discuss the implications of these results for preventive interventions to reduce adolescent problem behaviors.