The high school musical is a common activity for many high school students in the United States. This study presents a contextually rich historical analysis of the high school musical at one suburban school in western New York. The literature review consists of three major sections: the role of extracurricular activities in schools, the importance of music education, and an analysis of theater and drama programs in schools. The literature includes academic benefits of extracurricular activities, the social and emotional growth experienced by students in music and theater activities, case studies of productions, and analysis and criticism of show choices. This study is presented in two parts: document analysis and qualitative interviews. The document analysis includes review of past programs, newspaper articles, and other important documents to analyze the development and continuation of this particular school’s musical program. The qualitative interviews were conducted with key members involved in the history of the musical including past directors and alumni spanning the forty years of the production. Findings and discussion center around three major themes: the importance of having a strong musical theater program, dedication of the team and creating high expectations, and the ability to deal with challenges and manage transitions.