This article explores the interaction between popular culture, community-based education, and the establishment of a critically literate debate community, using the case of City Debate as one example of how critical literacy is embedded and taught through curriculum. Debate has historically been conceptualized as a structurally rigid space for traditionally academic youth (Fine, 2001); however, in the nontraditional space of the urban debate community, instructors and students used access points rooted in both popular culture and Black culture to engage students in deep thought about national policy and the ethics of actions (Cridland-Hughes, 2017; Warner & Bruschke, 2001). Using ethnographic methods, including participant observation and interviews (Merriam, 1998), document analysis (Prior, 2003), and triangulation, I examine the framing and implementation of one urban debate community, looking for how curriculum and pedagogy meet community critical literacy goals.