The purpose of this multiple case study was to examine the practices and perspectives of four music teachers who integrated popular music and informal music learning practices into their secondary school music programs in the United States. A primary goal was to understand music teachers’ process of enacting change. Data included 16 semi-structured interviews, eight school site visits and observations, documents, and a researcher journal. Findings revealed that teachers enacted change within micro-contexts—their classrooms. Teachers had an internal locus for change; they developed rationales for change and initiated curricular changes in response to a lack of student engagement, which seemed to stem from students feeling insecure in their musical abilities and disconnected from the content and pedagogy used in music classes. For the teachers in this study, the solution was integrating popular music and informal music learning practices. Thematic analysis revealed eight characteristics of effective teacher-initiated change in secondary music education: (1) holistic and gradual change processes, (2) teacher reflection and inquiry, (3) teacher autonomy, (4) enabling institutional factors, (5) use of a variety of supportive networks, (6) student-centered pedagogy, (7) teacher-selected professional development, and (8) a balance of structure and chaos and formal and informal learning.