The present study investigated the effects of parental monitoring, neighborhood risk, and racism experiences during early adolescence on adolescents' emotional and behavioral outcomes in high school. Five hundred twenty-two African American youth and their parents and teachers completed surveys about youth development over time. Consistent with our hypotheses, we found that neighborhood risk and racism had small and significant relations with anxiety, oppositional behavior, and conduct problems. Additionally, parental monitoring moderated the effects of neighborhood risk on behavior problems in both 9th and 12th grade, controlling for baseline problems. Finally, parental monitoring did not moderate effects of risk contexts on the development of anxiety problems. Findings are discussed with regard to implications for supporting effective parenting practices in high-risk contexts.