Through an ecological systems perspective, this study explores factors that influence successful academic achievement for African American males in at-risk settings. This qualitative study examines factors that contribute to the successful academic achievement for African American males from at-risk populations. The researchers explore African American boys’ lived experiences and what contributes to their success in school. Educators and counselors are able to encourage African American male engagement in academics by understanding the interconnectedness of lived systems. This study explores the interdependency of systems in the development of self-concept for these youth. Findings suggest the value of using a systems model and approach when working with African American males in public schools to improve post-secondary outcomes. These findings have implications for promoting academic success through family, school, and community involvement for African American males.