The aim of this chapter is to use Pierre Bourdieu’s theoretical tools to explore identity practices in relation to musical learning practices for working-class boys experiencing extreme levels of disadvantage. In order to expand our understanding, we draw on recent theorising around the relationship between gender identity and habitus (Adkins, 2003; Coles, 2009; McNay, 1999; Thorpe, 2010) to show how the masculine habitus was significantly altered through the musical practices of MCing and DJing. While boys are often characterised as reluctant learners (Jackson, 2003; Mac an Ghaill, 1988), this cannot be understood without reference to the immediate context, as habitus always operates in relation to field and is where identity is formed (Reay, 2010). In our analysis, we identify three interrelated key features to explore how identity is influenced by the learning culture. After a discussion of the usefulness of Bourdieu’s tools in our research, the chapter concludes with some of the implications of this analysis for working with disengaged boys.