Through case studies focusing on the generation of writers, artists, and intellectuals born in the 1950s and 1960s, I endeavor to trace and analyze the legacy of the Cultural Revolution in the cultural contradictions in China today. I will take the identity shift from "orphans of history" to "cultural bastards" as a site, and explore the ambivalent aesthetic and ideological relationships between this legacy and various cultural phenomena such as the vicissitudes of cosmopolitanism in Today modernist poetry (Duoduo, Bei Dao), the representation and critique of modem Chinese history in "the fifth generation" cinema (Chen Kaige, Zhang Yimou), the rise of "counter-culture" and popular culture (Wang Shuo, Cui Jtan), and a re-emerging cultural nationalism (Zhang Chengzhi). I will also ask how this legacy has affected western understandings of the aesthetic and ideological contents of contemporary Chinese literary and cultural outputs. In doing so, I hope to situate and illuminate the nuance and complexity of current Chinese cultural contradictions in a new historical and comparative perspective, that takes the legacy of the Cultural Revolution not just as a purely negative historical residue but also as an active cultural factor which continues mediating, affecting and problematizing, with regard to the problematics of historical discontinuity and cultural impurity, the process of China moving towards integration into a global system of economic and cultural production and consumption.