Forty years following Deng Xiaoping’s 1978 “Reform and Opening-up” policy, the Chinese Communist Party (CCP) has overturned longstanding assumptions that China’s integration with the liberal international order was a foregone conclusion. As the ruling Xi Jinping government continues to promote an alternative international system premised on its authoritarian governance model, liberal societies along China’s border—namely, Hong Kong and Taiwan—have emerged as points of fierce resistance to political, cultural and economic domination. While many accounts examining Hong Kong and Taiwan’s complex geopolitical relationship to mainland China, few primarily explore the culturally mediated ideals that underly the CCP’s authoritarian governance, or the mass movements resisting against them—notably the 2014 Sunflower Movement in Taiwan and 2019-2020 anti-extradition protests in Hong Kong. Drawing upon cultural texts from mainland China, Taiwan and Hong Kong, this dissertation aims to examine the moral foundations of the unresolved and ongoing political clashes between China and its contested border regions. I identify the ubiquity of scientism—mediated through early modern utopian literature—in early 20th century Chinese intellectual culture as providing a foundation for the rapid flourishing of Marxist political philosophy throughout China following the 1919 May Fourth movement. I then contrast developments on the mainland with those in Taiwan, demonstrating the role played by popular music, particularly rock and roll, in fomenting the island’s democratization and continued resistance against the CCP’s efforts to politically unify Taiwan with China. Finally, using Hong Kong cinema as a case study, I draw a link between the ambivalent attitude towards authority and ad hoc creativity of anti-government protestors in Hong Kong and the cinematic subculture that thrived in the latter decades of British colonial rule. Ultimately, this dissertation aspires to overturn Marxist-inspired critical frameworks that subordinate cultural texts to the economic “base,” and locate the origins of political resistance where it belongs, in the realm of culturally mediated ideas.