This paper, focusing on the protagonist Picaro`s pursuit of self-identity in a picaresque novel, a transitional genre to modern literature, compares Notes from the Underground, by the Russian author Dostoevsky, and Nalgae(Wings), by the Korean author Sang Lee. In so doing, a close examination will be made of Picaro`s self-identity and his quest for it, which later became the prototype echoed in the modern novel. In comparison with mainstream Western literature, Korea may have had many fewer picaresque novels throughout its literary history. When the country, however, was suffering under Japanese colonization, Korean modern novels were beginning to take shape, providing an opportunity for the emergence of a hotbed of picaresque novels - a genre of literature through which to express struggle against the oppressor and protection of the oppressed. Somewhat similar to Korea, Russia was also oppressed and humiliated in the process of modernization, and also became a fertile soil for picaresque novels. Thus, both countries seem to have had picturesque novels genre, if not quiet like those of the Western tradition. Picaro`s Notes from the Underground is of the very prototypical character that modern fiction writers often turn to when they write a picaresque story or fiction dealing with social evils and irrationality. The Picaro-like protagonists of both the novels of Dostoevsky and Sang Lee demonstrate what procedures they undergo in search of their self-consciousness, coming out from a closed space into the openness of freedom. Notes from the Underground, set in Petersburg, Russia`s capital in the 1840s through 1860s, talks about the issues of human reason and the logic of utilitarianism via a monologue of a solitary and critical visionary; Nalgae, with a setting of 1930s Seoul under the Japanese colonization government, deals with the problems of solitude in a large group and moral degradation, looking into the mentality of a person who is unsocial and eccentric, thereby suggesting experimention with a picaresque-style story. Picaro acts on his own volition, ignoring the wishes of others, but listening closely to the voice within him. Despite his confinement in a small underground cell, Picaro is firmly determined to move ahead for the release of his soul. Accordingly, the existential circumstances under which Picaro is placed are not only personal matters concerning Picaro himself but also a universal matter related to anybody living in a modern community. The language he speaks with every single part of his body is about progress in achieving humanism, overcoming discrimination, hope for liberty breaking away from the oppression of the hierarchical power, and a journey in search of true identity, shedding outdated tradition. Hearing what he has to say, we can understand his messages as the spirit of the times to reflect upon ourselves and renew our view of life. Consequently, by making a close observation of how we interpret Picaro, we can also reaffirm and recognize the prototype, leading us in the right direction as we live our lives.