In this study, we examine how race and racism impact the schooling of African American males by analyzing the first-person perspective of hip-hop superstar, Nasir "Nas" Jones. We selected Nas due to his unique yet prevalent educational trajectory and perspectives. Critical race theory is employed as a framework as well as notions of Sankofa methodology and literary analysis to investigate his music, documentaries, and an open letter whereby he critiques the public school system while providing academic ideas to engage and inspire Black students. Studies about Black males routinely focus on their subpar academic performance with the intention of "correcting" these behaviors. We utilize the experiences of Nas to reframe the conversation and provide nuanced insight into Black educational experiences instead of perpetuating recycled, bleak narratives. This article concludes with suggestions for educators to better serve African American males in the Pre K-12 academic context.