This article examines the particular strength of theater to raise questions about relations of gender and race. The authors consider the "rights" of youth and teachers in schools to use drama to critique their cultural contexts and connect these educational struggles to those of broader political, cultural, and social democratic life. The empirical work examined addresses the implications of challenging normative constructions of racial and gendered subjectivity in urban schools within the context of youth performances of both the social and artistic kind. The theater experiences and "controversial theater productions" discussed in this article challenge notions of "official multiculturalism" and ask questions about how--and to what effects--drama "rocks the boat" in contemporary struggles of social cohesion and social justice.