This study illustrates the ways in which the practices of two instructors in an arts-based, after-school literacy program serving Somali youth provide insights for teaching urban immigrant students. It draws on a qualitative self-study that examines the experiences and practices of the researchers in the development and implementation of a program called Pen 2 Paper 2 Power. It illuminates the difficulties of using culturally relevant pedagogy with immigrant youth, given the complexity of immigrant youth cultures, formed at the intersection of ethnic culture, youth culture, and popular culture. The research also examines the pedagogical implications of practicing culturally relevant hip-hop pedagogy with urban immigrant youth. (Contains 1 figure and 1 note.)