Calligraphy during the Song Dynasty (960-1279) and Yuan Dynasty (1279-1368) developed further in terms of the semi-cursive script (xing cao), but failed to achieve any further significant progression in regular script and wild cursive script (kuang cao). However, calligraphy during the Song Dynasty was unique in that it was much more idiosyncratic.

The invention of a movable printing technique by Bi Sheng around 1045-1048 during the Northern Song Dynasty (960-1127) had significant bearing on the development of calligraphy in two aspects: easy access to models of calligraphy, which facilitated in making Wang Xizhi and Wang Xianzhi’s calligraphy the absolute paragon to aspire to for calligraphy practitioners; and a diminished practicality for the role of calligraphy against increasing aesthetic emphasis and diversified styles practiced by a vast number of calligraphers.

Among the Song Dynasty calligraphers, Su Shi, Huang Tingjian, Mi Fu and Cai Xiang were the most notable and were collectively called, "the Four Best”.

Zhao Ji (1082-1135) is the most famous and accomplished artistically inclined emperor in Chinese history. He created the unique “Slender Bronze” style, or shou jin shu.

Of all the Yuan Dynasty (1279-1368) calligraphers, Zhao Mengfu was the most accomplished and ranked alongside Yan Zhenqing, Liu Gongquan, Ouyang Xun of the Tang Dynasty as the “Four Best Kai Shu Masters” of all times.