In the face of globalization, speed communication, and the mashing up of once clearly drawn borders, it seems both pertinent and constructive that music education philosophers make use of comparative frameworks to make sense—and make new sense—of educational and musical events, products, and interactions. However, comparison that is merely analytical, self-centered, and attempts to valuate, categorize, and create hierarchy or contradistinction, might be not only scholastically inept but also politically irresponsible. Philosophical investigation based upon “comparative cosmopolitanism” is interested in “difference that remains different” as a positive element and attentive to the ways in which we come to understand said differences. Therefore, this view is committed to philosophic enterprises that consider creativity, risk, and difference to articulate “forms of fundamental critical self-reflection that extend to the ‘scaffolding of our own thought.’” The goal of this article is to present an introductory reasoning for placing a comparative approach side-by-side a cosmopolitan framework, exemplifying its usefulness to philosophical work in and for music education.