Lee Nan-young is one of Korea's most famous female singers of Japanese colonial period, who sung a well-known popular song, "the Tears of Mokpo". Since liberation, Lee has been consistently interpellated as a code of nationalistic loss during the Japanese colonial rule, represented by the lyrics of her song "the Tears of Mokpo". Her musical ego had been always prescribed and defined by external forces even after liberation, and she had to accept it as herself. Though it may be the part of entertainers' common destiny, Lee had no choice but to embracing her fate in a self-destructive way, involved in cultural political power relationship between center and periphery, going through times of Japanese imperialism, the Korean War, and the era of harsh ideology of the Cold War. In this paper, I want to show the points on which Lee Nan-young's private desires were distorted or frustrated by the contradictory systems of reality. Her persona, interpellated in disparate and over-layered ways by demands of rapidly changing modern lives, had been repeatedly twisted and finally reached self-destruction. It may belong to her tragic personal affairs, but her innermost private experiences(her persuit of desires and loss of self, and hardship of life originated in her husband's being abducted to North Korea, etc.) are likely linked to those of Koreans in general who commonly went through Japanese colonial rule and modern Korean history stained by the tragic war. Lee Nan-young's songs and her successes and failures as an entertainer represent those linking points in a fragmented and metaphoric way.