This article explores how philosophical development proceeded through the practice of textual commentary, one of the major features of the Chinese philosophical tradition. This view of the history of interpretation in Chinese thought has hitherto not been addressed, though many articles on Chinese hermeneutics have been published. Most important Chinese philosophers constructed their new theoretical systems in the course of working out their annotations of early texts rather than by directly writing their own books and essays. Two key examples, Wang Bi and Guo Xiang, significantly set out and developed theories that would anchor Neo-Taoism (Wei-Jin Xuanxue or the mystery school) in their reinterpretations of the Laozi and Zhuangzi, respectively. Furthermore, Zhu Xi elaborated his impressive philosophical system in his commentary on the Four Books. The Chinese commentary practice is different from a general reinterpretation of a text because, as commentators, philosophers are supposed to explain the "original Meaning" of the text sentence by sentence and piece by piece, not to read into it their own divergent ideas. But there are two conflicting orientations in this hermeneutical activity: one bent towards ancient texts, the other towards contemporary needs and innovation. Both these oppositional orientations are always embodied in complete commentaries, which represent a certain mixed position between the historical-textual orientation and the current-creative orientation. Thus the conflict between these orientations can be detected retrospectively within these works. This article will demonstrate how these two orientations play out through two examples, namely, Wang Bi's commentary on the Laozi and Guo Xiang's commentary on the Zhuangzi. The article argues that Wang's work exemplifies an orientation basically following the direction of the original text, while Guo's work exemplifies one that is essentially concerned with contemporary issues and personal innovation.