Indigenous youth are disproportionately impacted by homelessness in Canada. Little is known about Indigenous youths' lived experiences of homelessness and the dominant methodological orientation in related research uses quantitative research methods. There have been calls for increased engagement in qualitative and arts-based research methods. In this article, we answer this call through exploration of two key issues at the intersection of Indigenous youth, homelessness and arts-based research: (1) theory and (2) method. Using thematic analysis of interviews conducted with youth in an applied community theatre project, this study identifies seven conceptual themes related to youth experiences with homelessness, and nine methodological themes related to decolonizing arts-based research. We explore the entangled relationship of applied community theatre and decolonizing methodologies with youth, considering what is contentious, multifaceted and complex about this relationship.