Through a literary-theatrical reading of international legality, this Article challenges the “settled script” produced by international legal scholars to frame and assess the legality of two historical events—the Grenada Revolution (1979–1983) and the U.S. Invasion of Grenada (1983). It does so by reading the Cold War as a sensibility performed by these scholars, one that recognized the operation of rival international legal orders and one that crafted a different script—Cold War Customary Law (“CWCL”)—to decide questions of international legality in a Cold War context. In addition to offering a new way to read the Cold War and international legality, this Article argues first that it is important to uncover this parallel and competing script of international legality operating at the time, and not dismiss it as unrelated political or ideological discourse, as it clearly influenced the interpretive logic and reasoning practices international lawyers deployed to frame what constituted legality in international law. Second, it argues that this Cold War sensibility in international legal scholarship on intervention and revolution predated the events in Grenada, and that if a different theatrical mise en scène is adopted—one which eschews “the short durée” or “evental history” of the settled script—this sensibility can be understood as being both continuous and discontinuous with rival imperial forms of international law operating in the Caribbean across time and place, where its discontinuities open up space to recover revolutionary Caribbean subjects of international law and a sensibility of shame in the present.