ABSTRACT. Objective: Past research has associated childhood characteristics and experiences with alcohol use at single time points in adolescence. Other work has focused on drinking trajectories across adolescence but with risk factors typically no earlier than middle or high school. Similarly, although the connection between underage drinking and affi liation with deviant friends is well established, early risk factors for their covariation across adolescence are uncertain. The present study examines the infl uence of early individual and contextual factors on (a) trajectories across high school of per-occasion alcohol use and (b) the covariation of alcohol use and deviant friends over time. Method: In a longitudinal community sample (n = 374; 51% female), temperamental disinhibition, authoritarian and authoritative parenting, and parental alcohol use were assessed during childhood, and adolescents reported on alcohol use and affi liation with deviant friends in the spring of Grades 9, 10, 11, and 12. Results: Early parental alcohol use predicted the intercept of adolescent drinking. Subsequent patterns of adolescent alcohol use were predicted by sex and interactions of sex and childhood disinhibition with early authoritarian parenting. Additionally, childhood disinhibition interacted with parental alcohol use to moderate the covariation of drinking and deviant friends. Conclusions: These fi ndings highlight early individual and contextual risk factors for alcohol use across high school, extending previous work and underscoring the importance of developmental approaches and longitudinal techniques for understanding patterns of growth in underage drinking. (J. Stud. Alcohol Drugs, 74, 746-756, 2013)