Abstract: WU Bao’an (《吴保安》) is the first biographical legendary work in Ji Wen (Records of Curiosities《纪闻》) and tells the story of the friendship through thick and thin between WU Bao’an and GUO Zhongxiang. In the narrative adaptations of friendship by writers throughout the ages, this story exhibits a phenomenon of transmutation and transmission among various literary genres, including historical records, dramas, and dialogic fictions. The story itself possesses the elements for successful adaptations across multiple genres. The process of historical recordization reflects the continuation of the historian’s pen by the author of romance, and the changing concept from parallel prose to prose during Tang and Song Dynasties. The theatrical adaptation, through the use of symbolic objects and contrasting roles, sets the stage for the transformation from refined to popular drama. The adaptation into dialogic fictions highlights the novelists’ efforts to reconstruct the ethical order of Confucianism amidst the social chaos of the late Ming Dynasty.