This study explores a psychosocial concept coined by the author referred to as "Urban Critical Literacy" (UCL). UCL is an emergent four-step strategy employed by five African American young men as they navigated their cultural worlds of home and school in an urban setting. Critical literacy is the theoretical conceptual framework that underlies this research. Data collected through individual and group interviews and direct observations of home and school are further grounded in constructivist theory to help guide the investigation and documentation of how the participants used UCL. The findings revealed that the participants employed UCL as a strategy to help navigate and negotiate peer pressure, styles of communication, dress, and stereotypes as well as school personnel's unfavorable perceptions of them that can potentially impede their school success. The young men critically identified and reflected on these issues in ways that empowered them to make responsible decisions without jeopardizing their academic goals.