The article aims to rethink the pluralistic intellectual currents and social changes of the last centuries in China: How literati reacted to the historical changes, the economic developments, the collapse of the hierarchical order, and the social mobility from the end of the Ming to the middle of the Qing dynasty. Urbanisation, the great silver inflow, the acceleration of trade, and social mobility raised new challenges to the orthodox view of the world and to Neo-Confucian norms. These new attitudes of the Chinese literati—which can be inferred both from literary and philosophical works—uncover new attitudes in the mental structure of the intellectual strata of the time. In the history of ideas we notice a progressive detachment from the orthodox view of the conflictual relationship between principle and desires, especially in the ambit of the Taizhou school. The elaboration of a new anthropological mindset aimed at the rehabilitation of passions and desires culminated with Li Zhi. This trend went on in the Qing period, from Wang Fuzhi to Dai Zhen. In literature, a similar trend, the so-called “cult of qing ,” can be found with the moral justification of emotion-desire (establishing emotion as a genuine and active source of virtue), and with the vitalistic identification of emotions as the source of life and reproduction. Another indication of change is the challenge of common and accepted truisms through the praise of “folly” in real life situations and literary works: To be “crazy” and “foolish” became a sign of distinction among certain intellectual circles, in contrast with the pedant orthodox scholars and officials and the vulgar nouveaux riches . The unconventional character of the anti-hero Baoyu is emblematic, with his aversion for any kind of official ceremony and convention, his abnormal sensibility and impractical and na?ve mentality, and his consciousness of being different from others. The crisis of the established ladder of values can be seen in the exaltation of “amoral” wisdom and in the presentation of various dimensions of love, from the idealistic sentiment of “the talented student and the beautiful girl” to the metaphysical passion that overcomes death, and to the minimalist concept of “love is like food” in a carpe diem perspective. And finally another challenge is exemplified by Yuan Mei’s reflections on the concept of Heavenly Mandate, retribution, human responsibility, and historical constructions by resorting to “abnormal” phenomena to uncover the absurdity of reality and unconscious imagery. His questions testify the polyphonic debates of the late imperial China, besides established conventions and Neo-Confucian orthodoxy.