As the incorporation of popular music into secondary and university learning spaces continues to expand, of particular interest is how ways of learning and teaching popular music might be enacted in a school environment. Well-meaning teachers, music education organizations, and corporate entities, in an effort to codify these ways, continue to explore various methods of operationalizing popular music to fit within the paradigmatic structures and core narratives of music education. Given this climate, what might teachers employing popular music gain from developing a better understanding of the diverse ways popular musicians learn, create, perform, and teach?This narrative and multiple case study considers the stories of three professional musicians who, at some point in their performing career, also became music teachers. By exploring how the orientations (i.e., experiences, knowledges, beliefs, and practices) of these professional musician~teachers were cultivated through the diversity of their experiences encountered both on and off the gig as well as in and out of classroom, this study explores how these individuals blended their biographical pasts as professional musicians with their developing teaching practices in the popular music-focused classroom. Based on this exploration, the following questions guided this inquiry: 1) What are the individual orientations of professional musicians who also teach in popular music-focused learning spaces in secondary school settings?, 2) Where and how did these professional musician~teachers acquire their orientations during their time as student-musicians and as professional musicians?, 3) How do these professional musician~teachers approach teaching popular music in popular music-focused learning spaces in secondary school settings?, 4) How are their orientation(s) evident in their teaching practices?, and 5) How did their orientations evolve to include their newfound experiences as they developed their teaching practice? Findings indicate these professional musician~teachers: 1) learned to teach by teaching and, through this process, developed a unique blend of content and pedagogical knowledge, 2) adopted a flexible perspective of classroom structures and teaching approaches and, 3) transferred evaluative skills gained from their experiences as professional musicians into the classroom as they sought out ways to improve their teaching practice.