The practical reality for far too many urban schools is one that reflects the despair, dire socioeconomic situations, and a complex cultural ethos of numerous neighborhoods and countless youth. Thus, a more rigorous analysis and critical appreciation of youth is necessary because their issues are complex, multifaceted, and delve deeper than what we might see on television or hear in trite superficial conversation. This context creates quite a daunting situation for educational leadership in urban schools. This article has three purposes: (1) to provide insight into urban youth culture, specifically examining Black popular culture; (2) to propose a framework for analysis of youth culture (i.e., cultural collusion); and (3) to present considerations and implications for educational leaders in an era of high-stakes testing, accountability, and No Child Left Behind.