The lack of strong literacy skills and practices among students is perhaps the clearest indicator that the education system continues to leave millions of children behind. To advance the reading, writing, and speaking skills of middle and high school students, this study examines a professional development model that brought trained community-based poets into the classroom to conduct weekly writing workshops. Over the course of two years, poet-mentor educators worked alongside 30 English Language Arts and Special Education teachers, reaching over 800 students. When the literacy program entered its second year, issues of propriety and language usages unveiled deep rifts between who students were as individuals and who educators wanted them to be as learners. The literature on multiple literacies and cultural relevancy helped frame the professional development within a larger movement to bring student voices and experiences into the curriculum (e.g., Gay, 2000; Ladson-Billings, 1994, 1995; Mahiri, 1998a, 1998b), but even this scholarship does not address the contentious interplay between student self-expression, conformity, and academic achievement. So what happens when students' poetry embodies inner-city street vernacular and volatile subject matter that offends teachers? To address this concern, my research analyzes how to use spoken word poetry as a form of critical literacy development and empowerment within the confines of school.