Parents play an important role in delaying adolescent tobacco use, particularly through role modeling, parent-child relationships, and monitoring. Although these intrafamilial processes are relatively well documented, few studies have examined them among urban, Black mother-son dyads. Using data from 526 mothers and their adolescent sons living in public housing communities, this secondary longitudinal data analysis examined how parenting influenced adolescent boys’ tobacco use. Although mother-son closeness and maternal intention to communicate to sons about not smoking reduced the risk of tobacco use among Black adolescent boys, maternal role-modeling, particularly past 30-day use, emerged as the most significant predictor of tobacco use. Research findings highlight the need to shift from individual-level interventions toward strategies designed to change family system-level behaviors.