This study examined the relationships between youth and parental sensation-seeking, peer influence, parental monitoring and youth risk involvement in adolescence using structural equation modeling. Beginning in Grade 6, longitudinal data were collected from 543 students over 3 years. Youth sensation-seeking in Grade 6 contributed to risk involvement in early adolescence (Grades 6 and 7) indirectly through increased peer risk influence and decreased parental monitoring but did not have a direct contribution. It contributed directly and indirectly to risk involvement in middle adolescence (Grades 8 and 9). Parent sensation-seeking at baseline was positively associated with peer risk influence and negatively associated with parental monitoring; it had no direct effect on adolescent risk involvement. Parental monitoring buffers negative peer influence on adolescent risk involvement. Results highlight the need for intervention efforts to provide normative feedback about adolescent risky behaviors and to vary among families in which parents and/or youth have high sensation-seeking propensities.