The underrepresentation of Black males in college and university campuses has continued to raise alarming questions for parents, teachers, and policy makers. In this study I utilized Intersectionality theory to examine Black males’ experiences in high schools in order to gain an understanding of the factors that impact their educational attainment and subsequent development of college aspiration. Based on 30 qualitative interviews with 10^th, 11^th, and 12^th graders and 30 interviews with their parents, this study examined familial and social contexts in relations to Black male students’ educational attainment. Four key findings revealed that, 1) young Black men had to deal with gender-specific racial discrimination on a daily basis by counteracting the prevalent negative images against Black males in mainstream American society, 2) peer pressure exerted positive influence in middle to high SES neighborhoods and schools; but showed negative impact on their educational attainment and college aspiration in low SES neighborhoods and substandard schools, 3) female headed households in particular did not necessarily have negative effects on Black male students’ educational attainment, and 4) private schools appeared to have better climates than public schools in inspiring Black males to higher levels of academic achievement and college aspiration. Policy recommendations were proposed to stimulate Black male students’ greater interest in college attendance and educational achievement.