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Despite decades of research on the black-white achievement gap, we lack an understanding of how gender and race intersect to influence educational outcomes and how this may vary in different contexts. The gender gap in educational attainment is highest among African Americans, with African American males having lower educational attainment than other groups. Using the National Longitudinal Study of Adolescent Health, this paper investigates how the level of family disadvantage of schoolmates in grades 7-8 (school-level index based on parents’ education, poverty status, family structure, and teenage parenting) relates to the educational attainment of African American males in early adulthood. How do patterns for black males compare with those for black females and white youth, after accounting for individual family disadvantages and other individual, family, school, and community factors? Results support the hypothesis that concentrated schoolmate disadvantage more negatively relates to educational attainment among African American males than females. The level of schoolmate disadvantage in 7-8th grades shows an increasingly negative relationship to high school graduation (versus dropping out or obtaining a GED) among black males but no relationship among black females, net of individual, family, school, and community factors. For the outcome of college entry, conditional on completing high school, highly concentrated schoolmate disadvantage negatively predicts college entry among both black males and females, but to a greater extent among black males. Black males attending 7-8th grade with the most disadvantaged schoolmates have a 50% predicted probability of graduating from high school and a 14% probability of entering college.