The correlates of adolescent sexual behavior and externalizing spectrum behaviors have been documented across a range of disciplines and include both genetic and environmental factors. Over the last 15 years, the dynamic interplay between genes and the environment has garnered increasing interest among researchers who study risk-taking behavior. In spite of this popularity, the racial and socioeconomic composition of much behavioral genetic research to date has been largely homogenous, based on middle- to upper-middle-class Caucasian samples. Consequently, the universality of many findings remains unclear, and the roles of key contextual factors related to race and social privilege remain largely unexamined. To address these gaps, my dissertation will include three empirical studies, leveraging a range of biometric and structural equation modeling techniques to address three research questions. Each question builds in succession toward the overarching objective to better understand the contextual roles of racial stratification, social class, and chronic stress and trauma in relation to individual differences in adolescent sexual health and externalizing spectrum behaviors.