Modernism has dominated the version and interpretation of Chinese classics for nearly a century. Because of this universal tendency, many contemporary scholars are inclined to characterize random by freedom. Nevertheless, freedom is a fundamental notion in the West. In contrast, random (xiaoyao) is an important and typical notion for Chinese. They represent the deepest differences of basic beliefs between sophisticated Chinese and the educated Western. Obviously, random cannot replace freedom equally. This paper aims at taking an examination and an evaluation about the serious misunderstanding mentioned above. It includes the following important arguments: (1) Random is not merely a humanistic concept, especially not an anthropocentric concept. (2) Random is always involved in the context of non-dualism of human being and Nature. (3) Random is an environmentally friendly concept, but freedom is not. Freedom is a kind of individualist priority, but random is not. In fact, random opposes to the meaning of freedom in many aspects. (4) The modernist reading of random overlooked the ontological implication of random. (5) We need to trace back random into Taoist philosophy. (6) We can develop a discourse between Taoism and postmodernism after we have traced back random into Taoism once more. (7) Random means an approach to the ultimate pleasure; freedom is not able to help the man to realize the ultimate worldly good. Yet, freedom of man can serve as an instrumental mean for perennial, integral eco-happy inside the range of principle of random. Modernism has dominated the version and interpretation of Chinese classics for nearly a century. Because of this universal tendency, many contemporary scholars are inclined to characterize random by freedom. Nevertheless, freedom is a fundamental notion in the West. In contrast, random (xiaoyao) They represent the deepest differences of basic beliefs between sophisticated Chinese and the educated Western. Obviously, random can not replace freedom equally. This paper aims at taking an examination and an evaluation about the serious misunderstanding mentioned above. It includes the following important arguments: (1) Random is not merely a humanistic concept, especially not an anthropocentric concept. (2) Random is always involved in the context of non-dualism of human being and Nature. (3) Random is an environmentally friendly friendly concept, but freedom is not. Freedom is a kind of individualist priority, but random is not. In fact, random opposes (4) The modernist reading of random overlooked the ontological implication of random. (5) We need to trace back random into Taoist philosophy. (6) We can develop a discourse between Taoism and postmodernism after we have traced back random into Taoism once more. (7) Random means an approach to the ultimate pleasure; freedom is not able to help the man to realize the ultimate worldly good. Yet, freedom of man can serve as an instrumental mean for perennial , integral eco-happy inside the range of principle of random.