"The Unauthorized Biography of Li Shishi" depicted life stories of Li Shishi by means of legendary manners, and it provided judgments of characters at the end of the story. It not only passed judgments on right and wrong of characters, but also voiced concerns about current politics and social affairs. The book stressed that history was a mirror and everything would be obedient to justice. The image shaping of Li Shishi in the book was mainly set off via the interaction with other characters, and her personal traits of wit and charm, indifference to wealth, and great courage were fully expressed. In particular, born in a whorehouse and raised by her snobbish granny Li, Li Shishi still possessed noble and pure personality; it was commendable that she could live a chaste life in a hostile environment. Although it was fortunate for her to be appreciated by Emperor Song Huizong afterwards, she became a tribute that Zhang Bangchang proffered to Jing’s master when Jin’s armed force invaded Northern Song Dynasty. Eventually she died a glorious death, and it outstood her moral sentiment of patriotism and contrasted to Emperor Song Huizong’s fatuousness. This book implied critics that the monarch and all the males failed to defend their nation and Southern Song Dynasty recommitted the same weakness of Northern Song Dynasty. It afforded salutary lessons for the rulers and provided the sarcastic implication from its characterization. Compared to other works, the author of "The Unauthorized Biography of Li Shishi" has created a totally different image of Li Shishi under the prevalence of Neo-confucianism in Song Dynasty. Also, this book manifested the author’s unique characterization technique and his contribution to the development of legendary novel in Song Dynasty.