© 2013, © The Author(s) 2013. Within the adolescent risk behavior literature, questions remain about relationships among behaviors in early adolescence, gender, context, and negative social and health outcomes. Additionally, little attention has focused on trajectories of adolescent risk behavior among impoverished African American youth. Using data from the Mobile Youth Survey, a multiple cohort longitudinal study of adolescents living in impoverished neighborhoods, we have reduced gaps in the literature by identifying trajectories of alcohol use for males and females separately as a function of early initiation of alcohol use. Our findings indicate that early initiation of alcohol use predicts escalating use at least through age 17. Results are especially notable for females who begin drinking before age 12: They drink significantly more than any other group at age 12 and their trajectory remains the highest through age 17. Our findings about the escalation of drinking have implications for efforts to improve the lives of impoverished adolescents.