While the criminological literature has devoted great attention towards examining prison programs and interventions, the research has largely overlooked arts-based initiatives within prison. To gain an understanding of the impact that prison theatre has on the lives of criminalized individuals, this thesis represents a case study on Canada’s only inmate-run prison theatre, William Head on Stage (WHoS). Through qualitative interviews with 15 incarcerated WHoS participants and 6 former WHoS participants, this study explores the experiences of individuals with this long-standing theatre initiative. By implementing an integrative conceptual framework that captures the prison backdrop to which prison theatre operates, this study draws on Goffman’s (1961) total institutions as well as conceptual understandings around the prison culture (Ricciardelli, 2015; 2014b). Through the analysis of the participants’ experiences, the emerging themes in this study collectively reveal how the impacts of WHoS stem from the contrasting nature of prison theatre to both the structural and social systems of prison. While this research study helps substantiate the significance of arts-based initiatives like WHoS, it also helps bridge the gap within the literature between the arts and criminology.