Queerness and Chinese Modernity examines the explosion of alternative sexuality in the People's Republic of China (PRC), Taiwan, and Hong Kong. Drawing on methodologies in Chinese cultural studies, East Asian and area studies, and queer theory, I propose an inter-regional, East-East transnational approach that juxtaposes queer literature, films, new media, and cultural politics in the PRC alongside cultural productions in post-Martial Law (post- 1987) Taiwan, and Hong Kong before and after the 1997 postcolonial handover. I locate particular dialectics of queer time and space that dislocate the multiple hegemonic forces of normative kinship, nationalism, transnational capitalism, postmodern claustrophobia, and new forms of discipline and control in the convergence of old and new media. Chapter 1 studies female writers like Chen Ran, Chen Xue and Huang Biyun who have all written narratives about "the family" that imagine lesbian subjectivity. I argue that these writers radically challenge the nationalist ideology of family's cooptation under the state. Chapter 2 travels across time in order to study the transgendering of a misogynistic Ming dynasty folklore into modern genres of perverse femininity. I point to various modern adaptations of The Legend of the White Snake that rewrite gender regulatory divisions and provide cross-historical methods for reading transgender embodiments. In Chapter 3, I posit "inter-temporality" in wide-ranging filmic traditions and argue that non- normative gender embodiments mark productive sites for disrupting the homogeneous time of the nation. Chapter 4 explores films by Yonfan, Cui Zi'en, and Tsai Ming-liang that provide sexual remapping of postmodern cities. I argue that "being in the closet" is crucially linked to the postmodern experience of claustrophobia. Chapter 5 demonstrates that new media can re-empower the state's ability to track dissident sexual cultures while at the same time allow new possibility for redefining "the public sphere." I draw on Foucault's theory of the repressive hypothesis and Deleuze and Guattari's concept of assemblage to theorize our contemporary age as "transmedia assemblage." Through four case studies, I track the double bind of control and freedom in the age of media convergence. Overall, this dissertation locates vibrant queer transnational connections between multiple Chinese and Sinophone cultures