Background/Context A good deal of research has been written about the problems and challenges facing Black male youth in their educational endeavors, ranging from academic performances, aspirations, and outcomes to student–teacher relationships, social experiences, and identity development. Statements calling for more Black male teachers abound in current educational discourse, and a number of studies have focused on their experiences in teaching, their pedagogical practices, and their role within the school setting. However, little attention has been given to how Black male students experience their learning and relationships with Black male teachers—the very people who are supposed to benefit from this adult presence. The present study investigates Black male students’ experiences with Black male teachers at a single-sex urban secondary school. Purpose The purpose of this study was to understand Black male students’ experiences in an all-male learning environment, with a particular emphasis on the role of Black male adults in their schooling experiences. Participants This study focused on the schooling experiences of 20 college-age Black males who all attended the same single-sex public high school. Research Design Qualitative research methods were used in this study. In particular, data from in-depth interviews explored students’ narratives about how they experienced and made meaning from the all-male schooling environment. Findings Findings suggest that the students conceptualized adult Black males at their school as otherfathers based on their pedagogical practices, care and concern, and support. First, students expressed their need or desire for male teachers in their secondary schooling experiences. Students identified Black male adults as significant contributors to their development. Second, learning from Black male teachers was valued highly by students because these experiences provided them with insider perspectives and key insights on being Black and male. Students were exposed to opportunities to learn about how race and gender could matter in their lives. Finally, engaging with Black male adults in their schooling experiences provided students with unique opportunities to learn more about themselves. Students’ learning enhanced their critical consciousness and connected to their racial and gender identities as well. Students attributed much of their success and personal development to how Black male teachers engaged in otherfathering—expressed as holistic care, support, parenting, modeling, and life coaching. Recommendations Implications and recommendations for educational researchers and practitioners to better understand how Black males matter in the lives and schooling experiences of Black male youth are discussed.