The purpose of this study is to raise questions by exploring, writing, imagining, and telling the musical life stories of Billy Cioffi. Billy Cioffi is a professional musician, band leader, private teacher, professor of English, and, formerly, a musical director for acts such as Chuck Berry, Del Shannon, and others. In this document I explore the life of Billy Cioffi with the following questions in mind: 1. What might Billy's musical experiences, expertise, teaching, and learning teach us about music education? 2. What might the story of Billy’s musical life cause us to question about institutional music education? 3. How might his story trouble beliefs and perceptions about music teaching and learning? Prior to Billy’s story, which appears as a novella, I raise questions about popular music, its histories, and its place in music education contexts. Following the novella, I invite readers into four different “endings” to this document.