Youth's free time is an opportunity for profound development of skills, attitudes and behaviors. Research on this topic has focused on middle class or White communities. The current study, conducted with an urban, low-income sample of 138 African American adolescents, examined associations between parental monitoring, support of autonomy and control, and adolescent amotivation, ability to restructure, and planning and decision-making skills in free time with adolescent substance use, delinquency, school attachment, and academic achievement. Data were collected in 2008-2009. Parental monitoring had the clearest association with outcomes, although all parental behaviors and free time variables were important. Understanding these associations in this population informs efforts aimed at promoting success of African American adolescents and preventing delinquency.