This qualitative study examined the question: How can arts-based approaches facilitate transformative learning in a student teaching seminar? Two teacher educators facilitated a supplemental and voluntary arts-based ST seminar that comprised six, two-hour sessions. Thirty-four student teachers participated over five semesters making use of Theater of the Oppressed and other arts-based activities to process dilemmas they faced in their student teaching contexts. Data included video recordings, photographs, journal reflection, participant artwork, and transcribed focus group interviews. Data analysis employed line-by-line coding to identify critical incidents. We offer examples where pre-service student teachers worked with a dilemma, examined their assumptions, engaged in perspective-taking, and in the process explored new possibilities. Engaging in embodied reflections, naming, imagining, and critically reflecting provided rich opportunity for constructing new ways of thinking and feeling, which could lead to transformative learning. Issues relating to the seminar environment like safety, starting with participants' dilemmas, and willingness to take risks and ownership in the learning process supported transformative learning in an arts-based student teaching seminar.