This study examined the longitudinal association between contextual stress and health risk behaviors and the role of protective factors in a community epidemiologically-defined sample of urban African-American adolescents (N = 500; 46.4 percent female). Structural equation modeling was used to create a latent variable measuring contextual stress (community violence, neighborhood disorder, and experiences with racial discrimination). Contextual stress in 8th grade was associated with aggressive behavior and substance use 2 years later for boys. For girls, contextual stress predicted later substance use, but not aggressive behavior. High academic competence and self-worth reduced the impact of contextual stress on substance use for boys. Implications for intervention and directions for future research on health risk behaviors among African-American adolescents are discussed. (Published Abstracts) Tables, figures, and references