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This study examines the learning experiences of four teaching artists (musical theatre) working in one school setting through a single case study design. Kolb’s (2015) experiential learning cycle provided a theoretical framework for developing the data collection tools. Data included (a) two individual 60–90-minute interviews with each teaching artist, (b) one 60–90-minute classroom observation for each teaching artist, (c) one post-observation debriefing, and (d) one individual 60–90-minute interview with the artistic director and theatre department head. Analysis led to themes of mentoring, student relationships, identity, and the influence of art on teaching. Suggestions for future policy implication and research including prioritizing the working conditions for teaching artists and studying teaching artists’ experiences in larger scale designs.