This article examines family, friend, and media influences on competent and problem behaviors in a sample of 1,174 urban minority youth followed over 6th, 7th, and 8th grades. Students completed annual surveys at their schools. Each of the contextual factors investigated was significantly associated with concurrent aggression and delinquency as well as changes in these outcomes over time. In contrast, parental monitoring was most often significantly associated with indicators of competence both concurrently and over time (e.g., from 7th to 8th grade). In addition, engagement with violent media contributed to decreases in academic achievement. Overall, findings indicate that family factors, specifically parental monitoring, as a target of intervention, would not only offset risk trajectories but enhance positive development. (Contains 4 tables.)