Influenced by the philosophy of Dao School, most ancient artists, through creating artworks, developed themselves to a status of “being free naturally”; this thoughts of Laozi and of Zhuang not only embodied the artworks but also became a important foundation in art creating. Laozi and Zhuang clearly defined the thoughts and concept of “being free naturally” to explain how the University works. It is till Wei Jen Period, the phrase “freedom” gradually transformed itself from a Laozi Philosophy note into a concept of Aesthetic. To a certain degree, the calligraphy art had combined the Freedom thinking. By using “freedom” as a theme for this text, the author tries to systematically prove the calligraphy theory in the time scale of 600 years, from Cai Yong in Han Dynasty (AC133-192) to Lu Yu in Tang Dynasty (AC733-804), summing up the conclusions: Culvert purpose from nature body、Artistic technique with psychology combination、Unconscious creation behavior、Critics to Calligraphy、Characteristics of Calligraphy Appreciating and qualification that a person innately possesses.