Using the framework of social literacies studies, this article illustrates the central role of pleasure as both the motivation for and result of rap composition. Drawing on ethnographic research conducted with four young adults who are part of a rap collective, the author identifies three key sources of pleasure in composition: (1) Discourse membership; (2) Self-expression and self-representation; and (3) Play. These young adults, aged 15 to 21, are part of the very demographic overrepresented in statistics of school dropouts and underachievement: they are urban, African American, and from low-income backgrounds. Their passion for writing belies the statistics, and will be recognizable to educators who have seen adolescents trading oral rhymes in school hallways and scribbling lyrics in their notebooks. This article contributes to the growing body of research on situated literacy practices, offers insights about the young rappers and writers in our midst, and highlights the importance of creating contexts for learning that speak to youths' experiences and motivations.