This paper examines the dramaturgy of the dramas written in the period of Japanese colonial power on the Korean peninsula, and which followed and propagandized the Japanese system. Such disposition is considered `pro-Japanese` in Korea. Pro-Japanese dramas appeared when Japan`s imperial desire got into its stride since the late 1930s, especially during the early 1940s when the `Theatre Contest` took place three times in a row. This paper has studied the dramaturgy of the three dramas that were rewarded for the excellence in that Contest, “The Chinese Date Tree” by Ryu Chi-Jin, “History” by Song Young and “San-Ha-Yoo-Jung” by Kim Sung-Gu. Their works have particular significance not only because they disseminated Japan`s political ideology of the time, but also because they inherited them to an artistic level. Moreover, these dramatists participated actively in the Korean theatre and therefore it is assumed that their dramaturgies have greatly affected the thenceforth theater world of Korea. “The Chinese Date Tree”, the first won production of the theatre Contest, compares the small land of Korea and the wide land of Manchuria. It rationalizes the Japanese colonial system then and prevails upon the fact that Japan`s desire of imperialism would avail itself. The second won piece, “History”, grapples with the conflict and compromises between Korea`s tradition and Japan`s newly established policies. “San-Ha-Yoo-Jung”, the third rewarded piece of the Theatre Contest, lyrically presents the desirable figures of the public during wartime by showing cooperation among the people. Consolidating the characteristics of the three dramas while researching their dramaturgies, first, they appeal to the emotions of their familial organization. Second, the basic conflict of their work are the opposing opinions of the new and the old, in other words, the Korean tradition and the newly established Japanese structure are handled by different generations. Third, which includes the first and the second attributes, points out that the new system and the ideas ultimately win and are consumed in terms of familial emotions. However, individualism and liberalism, which were the characteristics of the modern western world, were rejected. Last, the modern qualities compared to the modern times of the West which rest upon individualism has very much of totalitarianism. Looking at these characteristics, they are closely related to the fact that Korea`s modern qualities could not help being distorted. This is because satire or the tragic nationalism that developed during the 1920s and the 1930s, which through the period refracted to become an enlightening totalitarianism, family-centrism, corresponds with the locus of the modern history of Korea.