Cross-cultural understanding stands as one of the great pillars of multicultural education and yet rarely do multiculturalists provide a full account of what it is and how it takes place. This paper will serve as an initial investigation into the complex nature of cross-cultural understanding. Drawing on the philosophical hermeneutics of Hans-Georg Gadamer, I will layout the framework for a theory of understanding and provide a concept of culture that avoids the pitfalls of essentialism and instrumentalism. I will then raise, as the backdrop for my examination, the issue of authenticity in the hip hop world. This will allow me to put these hermeneutic theories to work by illuminating the interpretive process through which a hypothetical middle-aged teacher might go about gaining an appreciation for rap music to better understand his suburban students who, for him, embody hip hop culture. This phenomenological account of cross-cultural understanding will in turn raise thought-provoking questions about human agency, translation, and the various implications of cross-cultural understanding in the classroom. (Contains 10 notes.)