The importance of positive leisure experiences within the developmental process is welldocumented for middle class youth of European descent (Caldwell et al., 2004; Feldman & Matjasko, 2005; Kleiber, Larson, & Csikszentmihalyi, 1986; Sharp et al., 2011). At the same time, there is ample evidence that free time, if not used in constructive ways, can be a fertile ground for problem behavior such as substance use or vandalism (Caldwell & Smith, 2006). There is far less evidence about the role of leisure time for African American youth, particularly regarding developmental processes leading to academic success or behavioral problems (Boyce, Robinson, & Richards, 2011; Fisher et al., 2002). Such research is important given that these early experiences may cumulatively lead to academic, economic, and personal success, or future problems (Caspi & Silva, 1995; Ford & Schroeder, 2011) that are disproportionately prevalent in this population (Rodriguez, 2013). Furthermore, research on the mechanism by which parenting behavior influences children's free time within a low income, African American population is extremely limited.Given the likely importance of the free time context in African American adolescent lives and the important role parents play in structuring and monitoring free time, the current study examines the linkages among five sets of variables: parenting behaviors, adolescent free time motivation and skills, school attachment, academic performance, substance use and delinquency in an urban, lowincome African American sample. Three models are tested examining potential causal mechanisms of how parenting behavior influences both risky and positive behaviors of youth through their free time experiences.PARENTING BEHAVIORS AND THE ADOLESCENT FREE TIME EXPERIENCEParenting behaviors are strongly associated with adolescent experience and outcomes associated with free time (Hutchinson, Baldwin, & Caldwell, 2003). We posit that adolescent perceptions of parental monitoring, control, and autonomy support have differing influences on three aspects of adolescent free time experience: amotivation, ability to restructure a boring free time activity (restructuring), and planning and decision-making skills (PDMS).Parental monitoring of free time activities may be protective of adolescent substance use and delinquency (Crouter & Head, 2002), especially in unsafe (Pettit et al., 1999) and low socioeconomic status (SES) neighborhoods (Chuang et al., 2005). High levels of perceived parental monitoring also correlates with less boredom during free time, a risk factor for substance use (Caldwell & Darling, 1999; Caldwell & Smith, 1995; National Center on Addiction and Substance Use, 2003; Osgood et al., 1996).Parental support of a child's growing autonomy in free time correlates with many positive outcomes, including ability to restructuring and PDMS (Caldwell et al., 2004; Hutchinson, Baldwin, & Caldwell, 2003), less antisocial behavior, and not using substances (Caldwell & Witt, 2011; Hutchinson, Baldwin, & Caldwell, 2003; Mahoney & Stattin, 2000). Parental autonomy enables adolescents to be challenged, improve skills, and make decisions.Not all parental behavior, however, is related to positive outcomes. For instance, youth who feel their parents exert too much control (over-control) over their free time activities typically report more boredom and amotivation in their free time activities (Caldwell & Witt, 2011; Sharp et al., 2006), which places them at higher risk of substance use (Caldwell & Darling, 1999; Caldwell & Smith, 1995; National Center on Addiction and Substance Use, 2003; Osgood et al., 1996). Youth who perceive parental demands to be over-controlling report less internal motivation, less developed decision-making skills and understanding of how to structure free time without help (Caldwell & Witt, 2011). Therefore, understanding how well these associations generalize to African American adolescents could inform how their parents positively influence free time experience. …