Abstract: Chinese classical calligraphy theory set afoot and budded during the Han, Wei and Six Dynasties (202 BC-AD 589). Then in the Tang Dynasty, it was greatly developed into the in-depth and detailed analysis on writing style and spiritual connotation of the calligraphy from the former descriptive studies based on the theorist’s impressions, constituting an overall framework that involves the discussion on the four aspects — techniques, aesthetics, humanities, and philosophy — all concerning Chinese classical calligraphy. As a result, the systemic theory on Chinese classical calligraphy was completely formed in this period. Meanwhile, the calligraphic literature before the Tang Dynasty was also preserved. This paper makes a comprehensive analysis on the basic context and value of the calligraphy theory in the Tang Dynasty in terms of the establishment of Emperor Taizong’s and Wang Xizhi’s classic status, Li Sizhen’s proposal of “Yipin” (A term used to describe works of art that achieve transcendence), the contents and values ofTreatise on Calligraphy(《书谱》) and Zhang Huaiguan’s calligraphy theory, comments on the new style of the calligraphy practice in the prosperous middle Tang Dynasty, the teaching and learning of the writing techniques and brushworks as well as the “Character Theory” during the late Tang Dynasty, and the contribution of Zhang Yanyuan’s bookImportant Records on Model Calligraphy(《法书要录》). In closing, it points out that the systemic theory on Chinese classical calligraphy was constructed and elaborated during the Tang Dynasty, when certain important aspects of Chinese calligraphy theory including the calligraphy form, calligraphy style, and writing techniques were fully studied, while some of them would be further developed in the following Song Dynasty.