During the twenty years of the post-New Era, Chinese society has undergone tremendous changes in the fields of politics, economy and culture. Since the 1990s, urban vagrants have gradually become a social class that cannot be neglected, whose formation and development expose many social problems emerging in post-socialist China. This dissertation proceeds from a single idea: it is timely and of great importance to chart the artistic representations of city migrants in Chinese films. The study explores how, conditioned by the three forces of market, government and the West, the images of urban vagrants—a marginalized social class—are represented in Urban Generation films by examining film texts, the cinematic language, and the process of production, distribution and consumption. This study also aims to demonstrate that films dealing with artistic representations of vagrants pose a challenge to the mainstream discourse and ideology of urbanization and modernization in post-socialist China. Specifically, through discussing cinematic representations of various social groups (which fall into the category of vagrants), such as travelling artists, homeless youth, migrant workers, and city dwellers, this study attempts to reveal how the cultural traits of vagrants—subaltern, marginalized, rebellious and exiled—and the cultural phenomena of rock culture, urban demolition, body writing and subaltern travel are closely related to and influenced by social and cultural changes in the transformation period of China in the post-New Era. The significance of cinematic representations of vagrants, as shown in this study, lies in the fact that the subaltern voices from the lower class (either from vagrants or as represented by filmmakers) are constructive for the development of contemporary China.