Research links racial identity to important developmental outcomes among African American adolescents, but less is known about the contextual experiences that shape youths’ racial identity. In a sample of 491 African American adolescents (48 % female), associations of youth-reported experiences of racial discrimination and parental messages about preparation for racial bias with adolescents’ later racial identity were examined. Cluster analysis resulted in four profiles of adolescents varying in reported frequency of racial discrimination from teachers and peers at school and frequency of parental racial discrimination coping messages during adolescents’ 8th grade year. Boys were disproportionately over-represented in the cluster of youth experiencing more frequent discrimination but receiving fewer parental discrimination coping messages, relative to the overall sample. Also examined were clusters of adolescents’ 11th grade racial identity attitudes about the importance of race (centrality), personal group affect (private regard), and perceptions of societal beliefs about African Americans (public regard). Girls and boys did not differ in their representation in racial identity clusters, but 8th grade discrimination/parent messages clusters were associated with 11th grade racial identity cluster membership, and these associations varied across gender groups. Boys experiencing more frequent discrimination but fewer parental coping messages were over-represented in the racial identity cluster characterized by low centrality, low private regard, and average public regard. The findings suggest that adolescents who experience racial discrimination but receive fewer parental supports for negotiating and coping with discrimination may be at heightened risk for internalizing stigmatizing experiences. Also, the findings suggest the need to consider the context of gender in adolescents’ racial discrimination and parental racial socialization.