The world of global trademarks can be characterized in terms of three major shifts: first, a shift from national to global branding strategies; second, a shift from national and regional systems to harmonized international regimes governing trademark law; and third, a concurrent shift from local to transnational social movements that challenge branding and other corporate practices. The rise of transnational brands brings with it an attendant series of legal shifts in trademark law. Long considered the stepchild of intellectual property law, today, trademark law has morphed into a powerful global legal phenomenon, revealing a foundational shift from national and regional systems to harmonized international regimes governing trademark law. A unitary system of trademark registration is emerging. However, even if a system of harmonized registration becomes the new normal, territorial systems of trademark enforcement — not to mention constitutional protections for freedom of expression — vary widely. Here, age-old questions regarding sovereignty, human rights, and artistic freedom have also begun to play a role in modern trademark disputes, both domestically and internationally. This Article details how each of these areas are deeply intertwined with one another, and how they demonstrate the emergence of a broad phenomenon that I call trademark cosmopolitanism, which carries important implications for freedom of expression worldwide. In this Article, I refer to the phenomenon of trademark cosmopolitanism to broadly sketch out four trajectories of transnational activities, and their relationships to the various entities that play key roles in the global branding enterprise — namely, the consumer, the corporation, the politician, and the activist. The first set of activities involves what I call consumptive cosmopolitanism, and that refers to the purchasing and shopping practices of the global consumer and the ways in which these practices reflect a kind of globalized consciousness. The second set of activities, which are closely related to the first set, involves the emergence of a corporately-oriented cosmopolitanism that stems from the global corporate social responsibility movement. The third kind of activity, which reflects a more macroeconomic set of considerations, involves the emergence of an institutionalized form of cosmopolitanism, which refers to the variety of government and nongovernment entities that have emerged to facilitate the creation, enforcement, and protection of transnational brands. The final set of transnational activities, however, typify a more politicized form of trademark cosmopolitanism that focuses on challenging, rather than consuming, the power of branding and multinational corporations. The interplay between the global brand, the global antibrand, and the language of ethics, cosmopolitanism, and corporate social responsibility, with all of the legal differences associated with sovereignty and speech, I would suggest, is one of the paramount issues for trademark scholars in the future