Parental incarceration, poverty, urban violence, and drug use can be underlying factors of academic achievement gaps between Black urban males and their counterparts. These risk factors have the potential to position low-income urban students as struggling readers. Two qualitative case studies obtained from a larger mixed methods study illustrate exemplary after-school literacy engagements with Black urban adolescent males, each with an incarcerated parent. Two researchers, a counseling psychologist and a teacher educator, collaborated to create a strengths-based after-school program with culturally relevant literacy instruction as their primary objective. The 2 case study findings reveal the complexities of choosing culturally relevant texts, the need for motivation and engagement in order to build skills, and the fact that relationships are essential in the delivery of culturally responsive literacy instruction. The article concludes with recommendations for teachers working with at-risk Black adolescent males that focus on student empowerment, academic success, and building successful futures. (Contains 2 tables.)