Abstract This article brings forth the difficulties and possibilities of enacting the role of “Joker” from Boal’s (1979) Joker System—formerly called the poetics of the oppressed. The authors acknowledge jokering as an apprehensive performance of brokering, of bodies that matter and are matter, that can provoke anti-oppressive actions and reinscribe oppressions. As such, four backdrops are engaged to further the methodological, theoretical, and curricular/pedagogical force of jokering as a performance that unsettles the status quo: Latina/Chicana feminist theories used in mentoring, performance-based action research with middle-school students, professional leadership development for schools, and socio-technological analysis with theatre in online/distance education. Each example from our praxis illustrates how the roles of emerging researcher, mentorresearcher, and researcher-practitioner are performed and troubled (jokered) from different disciplinary and theoretical perspectives to foster social justice praxis and outcomes.