Although the number of calls to integrate Hip-Hop culture into school curricula is growing, little attention is being paid to the reluctance of teachers and administrators to forge relationships between the cultures of school and of youth. This article explores some of the difficulties inherent in the relationships between Hip Hop and schooling, including interpretive tensions between White administrators and teachers and African American youth, and argues that the very controversies surrounding rap music are central to its pedagogic value. The article draws on qualitative research from a 2-year classroom study in an urban high on a "spoken word" poetry curriculum which included rap music. (Contains 2 figures and 2 notes.)