Hypotheses concerning the extent to which adolescents' cognitions mediate the relation between parenting behaviors and adolescent substance use were examined in a panel of African American adolescents (N = 714, M age at Time 1 = 10.51 years) and their primary caregivers. A nested-model approach indicated that effective parenting (i.e., monitoring of the child's activities, communication about substances, and parental warmth) was related to adolescent substance use more than 5 years later. The parenting behaviors protected the adolescent from subsequent alcohol, tobacco, and marijuana use through associations with two cognitive elements from the prototype/willingness model: favorable risk images (prototypes) and behavioral willingness. Additional analyses indicated that these protective effects were strongest among families residing in high-risk neighborhoods.