The introduction to this special issue outlines comparative approaches to cultural representations of post/socialism in order to move beyond the term’s association with the Soviet Union, the unevenly aligned or nonaligned nations in Central/Eastern Europe (CEE), and the period between 1917 and 1990. The histories and afterlives of state socialisms, and socialist globalization in Asia, Africa, Europe, and the Americas, are at the center of ongoing geopolitical realignments toward a multipolar world. The introduction explores the framing of these shifts as a “new Cold War” between the West and the nations of China and Russia, whose autocratic regimes are associated with remnants of totalitarian state socialism. Like the official rhetoric of many postsocialist nations, these discourses dismiss the far more diverse and progressive legacies of socialism. The introduction inserts cultural representations of Left Internationalism, the Non-Aligned Movement, socialist reformism, and committed art into the fields of comparative literature and media studies to contribute to theories of ongoing transformations and to provide alternative imaginaries for more equitable futures.