Zhuangzian musical thought has been rarely discussed in history of musical thought, while Confucian musical discourse such as Sage originated music, Musical evaluation or hierarchy, and Musical edification, has been enjoying legitimacy. However, Zhuangzian musical thought has played a profound role in later periods, not only for some critical thinkers' works but also for state attempts to reconstruct court music in East Asia. In this paper, by taking instances respectively from Song dynasty in China and Joseon dynasty in Korea, I will examine how Zhuangzian criticism influenced and transformed Confucian musical discourse. On the one hand, Zhuangzian idea allowed later scholars to supplement and thereby enhance Confucian musical theory. On the other hand, the idea inspired them to explore new musical ideas away from orthodox Confucian basis.