This research includes a series of case studies predicated on life history methodology, including analysis of interview transcripts, e-mail exchanges, and artifacts that interrogate the juxtaposition of official school literacies and unofficial out-of-school adolescent literacy practices. This particular study deals with an academically low-achieving youth who became very involved and highly acclaimed in Spoken Word which includes, but is not limited to, hip hop. Although Spoken Word competitions (slams) have become increasingly popular amongst marginalized urban youth both in the U.S. and Europe, it is my finding that teachers are often unaware of their students’ participation in these highly sophisticated out-of-school literacy events. Spoken Word provides a forum to express opposition to dominant hegemonic discourses, including those of schools. The dilemma for schools is that it is through opposition that these marginalized communities gain agency; therefore, Spoken Word cannot merely be integrated into school curricula because to do so would be interpreted by youth as colonization, undermining their autonomy and agency. Conversely, the dilemma for youth is that it is typically only through the credentials offered by schools that access to dominant discourses of power can be achieved. I posit that ignorance of this dynamic is detrimental to both.