Music is a powerful process and resource that can shape and support who we are and wish to be. The interaction between musical identities and learning music highlights school music education’s potential contributions and responsibilities, especially in supporting young people’s mental health and well-being. Through the distinctive stories and drawings of Aaron, Blake, Conor, Elijah, Michael, and Tyler, this book reveals the musical identities of teenage boys in their final year of study at an Australian boys’ school. This text serves as an interface between music, education, and psychology using narrative inquiry. Previous research in music education often seeks to generalise boys, whereas this study recognises and celebrates the diverse individual voices of students where music plays a significant role in their lives. Adolescent boys’ musical identities are examined using the theories of identity work and possible selves, and their underlying music values and uses are considered important guiding principles and motivating goals in their identity construction. A teaching and learning framework to shape and support multiple musical identities in senior secondary class music is presented. The relatable and personal stories in this book will appeal to a broad readership, including music teachers, teacher educators, researchers, and readers interested in the role of music in our lives. Creative and arts-based research methods, including narrative inquiry and innovative draw and tell interviews, will be particularly relevant for research method courses and postgraduate research students.