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For more precise understanding of the literature of Lee Sang, an investigation of his essays is a prerequisite. The investigation can help identify the values that Lee Sang either rejected or searched for, which allows us to explore his consciousness in depth. Furthermore, the investigation is also significant in that it allows us to understand better the consciousness of modern man in general. Women is an important subject in Lee Sang’s essays. Lee Sang interprets women in the symbolic dichotomy of “whore” or “holy mother.” Lee Sang defines as “whore” those who engage in exchanges based on capitalistic value system. However, his aversion is closer to the hatred of the capitalistic aspect of the modern condition itself that forces him to perceive women as “whore.” Lee Sang represented as “whore” all tendencies for seeking materialistic values embedded in capitalism and expressed his renunciation of it. On the other hand, he used the term “holy mother” for women who are not polluted by such materialistic value of capitalism and respect the value of life and expressed his approval. There are two types of “weariness” that Lee Sang describes in his essays. One is the feeling of “numbness” resulting from the inundation of the repeated sensations produced by constant stimulations of capitalist society. This is clearly expressed in his essay Tokyo in which he describes his disappointment about the city of Tokyo, which was imitated by Seoul, when he visited the city in Japan. The other one is simply the “boredom” caused by not having enough stimulations. In his essay Weariness, Lee Sang expresses his attitude toward such weariness caused by boredom. Also, in his letter to Kim Kilim, he wrote that, compared to Tokyo, Seoul was closer to a farm village, which illustrates the relativeness of stimulations where one can only feel stimulated when one encounters a stimulation that is stronger than his previously experienced stimulations. In his essays, Lee Sang often shows his attitude toward the idea of the “crowd” and the “public,” the terms that represent social group in modern society. He calls the “crowd” the ignorant social group and feels humiliation and anger about the fact that they consist of the majority of people in modern society. On the other hand, he regarded as his true readers the “public,” which was an extreme minority at the time, who was capable of rational thinking. It is only the public who could understood his works. His strong anger toward the “crowd” is shown in his later confession that it even drove him to hate the idea of “minjok” and “family.” Later Lee Sang admits that it was an error on his part. However, he did not withdraw his negative attitude toward social group nevertheless.