In contrast the plethora of between-race studies in the extant literature that focus on well-known and documented disparities between White and African American students, this study was conducted to gain direct insight from resilient, African American boys who beat the odds and achieved academically despite being at significant risk for failure due to extended exposure to compounded social and educational disadvantages. The primary foci of this investigation were to broaden understanding of the gender-specific challenges to academic achievement that African American boys encounter in school, understand how they overcome those challenges to succeed academically, and identify school-level enabling characteristics that contribute to their success – each from their perspective. Using semi-structured interviews with eight African American middle school boys, the findings of this study illustrate how these students accomplished proficient on state assessments in reading and mathematics – a feat that 85% of their peers did not accomplish nationwide.