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In modern society, instead of the distinct and conflicting concepts of East and West, we now live in an era where various heterogeneous things coexist. In the 17th century, when the archetypal characters Don Juan and Yang So-Yu first appeared, they took on different meanings in different historical contexts, but in a society fundamentally homogenized in terms of lifestyle, they would be dialectically integrated and interpreted with new meanings. In particular, in modern society, which is suffering from the problem of creativity depletion, it can serve as a way out of the humanities crisis by creating a new meaning with entertainment and popularity. Unlike modern times, where it is interpreted as a prototypical character called a playboy, Yang So-Yu of his time was a person who fulfilled all his worldly desires and achieved the Confucian ideal of success and good fortune through a happy life with two wives and six concubines. Yang So-Yu’s affectionate behavior at the time was concretely embodied as a person who achieved the ideology and desires of the nobility. On the other hand, Don Juan became the epitome of an immoral playboy and the prototype of a character type that inspired many artistic genres, but as a rebel who wanted to live freely according to his own will during the Counter-Reformation era of the 17th century, he directly challenged social taboos. He is a man who conquered women. He is a playmaker who does not know true love and a rebel against society’s asceticism. Don Juan’s love affair with women’s chastity is an act that goes against social order, a bold challenge to social norms, and an expression of hostility toward religion. Despite these different historical backgrounds, the two main characters have different meanings as achievers and challengers in a reality full of contradictions and conflicts.