The rise of post industrial urban centers and global communication technologies has created a distinctive Urban Youth Culture (UYC) with roots in Black history and social activism. In the discourse on education and Black youth, UYC is rarely seen as a positive force promoting academic achievement and self esteem. Drawing on the voices of Black urban youth in an all-male high school mentoring program, this article offers an affirming view on the significance and pragmatism of UYC to a group of young men at an East Coast high school. Findings reveal that the young men related to and relied on UYC to help them negotiate school and establish positive academic and social identities for themselves.