Sociopolitical development theory asserts that critical social analysis informs prosocial behaviors. We suggest that one aspect of Black adolescents’ critical social analysis development is an oppression analysis, in which Black adolescents consider (1) the importance of race to they are, (2) their personal feelings about their racial group, and (3) the experience of oppression for minority groups. The current study examined oppression analysis as a latent construct among a sample of 265 Black male adolescents in Grades 7 to 10 from three suburban districts in the Midwestern United States. Structural equation modeling revealed that received parental racial pride messages, but not school-based discrimination experiences, predicted Black male adolescents’ oppression analysis. An oppression analysis and school-based discrimination had direct effects on prosocial behaviors. Racial pride messages had an indirect effect on prosocial behaviors through oppression analysis. In addition, an oppression analysis had an indirect effect on prosocial behaviors through social-emotional skills. This research offers insight into the role of Black boys’ critical social analysis among individual and contextual factors in facilitating positive developmental outcomes.