With Bronfenbrenner's (1977) ecological theory and other multifactor models (e.g. Pianta, 1999; Prinstein, Boergers, & Spirito, 2001) underlying this study design, the purpose was to examine, simultaneously, key variables in multiple life contexts (microsystem, mesosystem, exosystem levels) for their individual and combined roles in predicting adolescent risk-taking and goal-oriented behaviors. Predictor variables were parenting behaviors (parenting style, monitoring, and involvement), the risk-taking and goal-oriented behavior of peers, and religiosity (attendance, involvement, and importance). General media consumption was also explored. The participants in this study were 272 9th to 12th grade Caucasian and Arab-American high school students (124 males and 148 females) from a suburban public school district in the midwestern United States (Mean age?=?15.64). Results revealed several themes, including that peers appeared to have the primary role in explaining variance in risk behaviors, while parents have the primary role in explaining goal-oriented behavior. Religiosity contributed minimally. There were several noteworthy differences between the two cultural groups regarding which factors explained the most variance in criterion variables. Results are explored in more detail and implications for prevention and intervention are discussed.