The purpose of this paper is to identify the way in which two painting themes of women in old tales, titled Lady Wenji’s Return to China (文姬歸漢圖) and Lady Mingfei Leaving the Country (明妃出塞圖), were introduced into Joseon from China and came to be accepted by the literati of Joseon. This paper also aims to examine the use of visual imagery for political and social purposes, and the characteristics of paintings of old tales, which combine the genre traits of paintings of a woman of virtue and paintings of a woman of beauty. Cai Wenji (蔡文姬), heroine of Lady Wenji’s Return to China , returns to Han, While Wang Zhaojun ( 王昭君), heroine of Lady Mingfei Leaving the Country , leaves the Han Dynasty of China. Therefore, these two women are connected but symbolize contrary values. Most works of Lady Wenji’s Return to China and Lady Mingfei Leaving the Country introduced during the Joseon period were painted in the Song and Yuan periods, while their interpretations also reflected the thoughts of the two periods. For instance, literati of Joseon received Lady Wenji’s Return to China in relation to the principle of “Distinction between China and the Barbarians, ” and assessed Cai Wenji following the idea of Song-period philosophers Zhu Xi and Cheng Yi that wives should value chastity over life. Furthermore, the literati of the Joseon period regarded Wang Zhaojun as a political victim and a beautiful court lady who died young, which was the same interpretation as Ouyang Xiu’s in the Song period.