Music is a self-transformative process, practice and ethic. The co-mediation of music and the self represents an assemblage of distinct yet simultaneously occurring parts where contradictions can exist alongside their more pragmatic uses. In this dissertation, I note such an assemblage in the case of Rob "Fresh I.E." Wilson. Wilson's case provides a striking example of musical self-transformation in that his biography follows a trajectory from abusive conditions in Winnipeg's infamous North End during the 1970s, and a life centered around drugs and pimping in the 1990s, to its lyrical renunciation according to his newfound beliefs as he converted his hip-hop to Christianity and joined the ranks of Grammy nominees in 2003 and 2005. Yet music was not all good for Rob. Despite fame and influence, by the end of the decade, he was overwhelmed by the demands of a grueling tour schedule and the pressure to remain relevant. His rising self-doubt pushed him to suicidal ideation. And yet, despite successfully restructuring his musical practice, now independent of the music industry, Rob's Christian-themed hip-hop still situates him between the rock of the institutional church and the hard place of having to constantly build a following. The constantly evolving nature of the contemporary Christian music industry and hip-hop's unique conditions in Canada, combined with the church's refusal to accept hip-hop as a legitimate mode of worship and Rob's refusal to leave, creates a distinct set of challenges.

In this dissertation, I use ethnographic research methods to explore the ways in which Wilson negotiates such challenges. I employ biographical methods to trace his present practice to the conditions of his formative and educational years. Not to limit this study to my case's word alone, I use historical methods to trace the trans-national links between Rob and hip-hop as it has become institutionalized, and before that, to its roots in African American religious musical practices since modern slavery. Finally, I use critical social theory to assess the significance of Rob's musical self-practice to himself and his scene, within the whole of the cultural realm.