The Woodlawn Project 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) attending the Woodlawn public and parochial elementary schools and follows their progress through adolescence, young adulthood, and midlife. This continuing research centers on aspects of life particularly salient to African Americans such as family relationships, school, work, peer relationships, religion, community involvement, health, criminal behavior, and criminal justice interventions. Despite similarities in their early roots, individuals in this group experienced disparate pathways to adulthood. Results continue to stimulate discussions on the refinement in the design of early prevention programs and contribute to research and policy literature on health and well-being of African Americans.