General music class is a space for students to engage in honest dialogue and reflection about the societal, cultural, and historical contexts of music, even when the subject matter is difficult. General music teachers can support students by opening "courageous conversations" about race, culture, and complex histories as they intersect with meaningful repertoire. The purpose of this article is to provide music educators with repertoire ideas and resources to assist in the process. Selections from Rhiannon Giddens' album "Freedom Highway" are explored as a point of entry for dialogue about race, culture, courage, and justice in the secondary general music classroom. Songs about the Civil War, the Civil Rights era, and the Black Lives Matter movement are linked to inquiry-based strategies and the national music standards.