The Woodlawn Study explores risk and protective factors on the path to successful or troubled adulthood in a group of African Americans from the same disadvantaged inner city community in Chicago. In response to citizen leaders’ concerns about life course trajectories of children in the Woodlawn neighborhood, this program of research and intervention began in 1966 with essentially all first grade boys and girls (1,242) and follows their progress into adolescence, young adulthood, and midlife. This continuing research centers on aspects of life particularly salient to African Americans (family relationships, school, work, peer relationships, religion, and community involvement) and on health and behaviors and choices that are influenced by and affect these aspects of life. Despite similarities in their early roots, individuals in this group experienced disparate pathways to adulthood. Results stimulate and refine the design of early prevention programs and contribute to research and policy literature on health and well-being.