Li Shimin, Emperor Taizong of the Tang Dynasty, is a famous and outstanding calligrapher in Chinese calligraphy history, who exerted far-reaching effect calligraphy theory and aesthetics. He was the first to show worship to Wang Xizhi, practiced calligraphy theory, monitored the calligraphy schools and opened the course of calligraphy. Besides, his aesthetic ideology also properly interpreted the calligraphy fashion in the early Tang Dynasty. Calligraphy, education, theory went through the entire life of Taizong, all of these achievements are able to appropriately annotate his obsession with calligraphy.