This article situates educational leaders as prophetic critics in Black popular culture. These leaders merge cultural criticism with moral and political judgment, analyzing urban youths' lived experiences and representational practices as well as analyzing counter-narrative texts in Black popular culture that have implications for urban education. As new world "bricoleurs," these educational leaders use a multi-vocal, polyphonic approach in Black popular culture to disrupt a Western culture of homogeneity that is less culturally responsive to the dynamic struggles Black youth face in urban communities. In addition, as critical organic catalysts, they locate life-pressing public concerns within subcultural communities of resistance as relevant knowledge to organize a radical democratic politics in educational leadership.