This article links the connection between music and leadership, exploring ways to connect musical icons to teaching leadership theory and concepts. The authors utilize the relationship leadership model (RLM) and the leadership identity development (LID) model through case studies of Beyoncé Knowles-Carter and Taylor Swift. We provide questions to deepen the facilitator and learners' understanding of these pedagogical approaches. Recommendations and implications follow to ensure educators and practitioners are thinking through the many other approaches to help leadership learners develop through examples of music.