The aim of this paper is to put Nanking paintings in the context of political and socio-economic developments in seventeenth-century China and to explore their significance as a cultural phenomenon. The paper starts with a discussion of the emergence of a taste for the eccentric and its manifestation in Nanking paintings of the late Ming period. The interaction between artistic style and the chaotic world outside is also crucial to understanding Nanking's turn from nostalgic expressionism to archaism in the later half of the century. In this perspective, the stylistic development of such Nanking masters as Kung Hsien and Kun-ts'an can be reinterpreted, and the fall of the Nanking artistic tradition can also be related to the process of political and cultural reconstruction initiated by the newly founded Ch'ing government.