Socio-historical contexts are integral to both general and music educational practices. However, when music teacher education candidates ask such questions as, "How can we engage in musics outside of the accepted canon and talk about these issues in my class without being accused by parents or administrators of being "political?"" they restrict possibilities for engaging with context meaningfully. Yet students, in their complex and often sophisticated musical lives outside of the formal institute of schooling, carry out these kinds of discussions and understandings with ease and nonchalance. Using the companion lenses of critical race theory and antiracism education, this article explores the reluctance of some music educators to engage those socio-historical contexts deemed political within multicultural and world music, asking: Without such contextualization, how is cross-cultural or intercultural understanding possible? (Contains 2 notes.)