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We can say that shaping sorrow into a poem is a essential feature of Lee sung boo’s poetry. Sorrow is significant because it is substituted for Han which was ancient Korean emotion. Sorrow in his poems is a emotion of the intellectuals who align themselves with resistant mass to injustice government power. Sorrow, the emotion of the intellectuals is worthy because it consoles grief of mass. Then sorrow accompanies with shame. Intellectuals have a sense of shame when they observe themselves. The shame makes them deny their worth to exist and write a literary work. To overcome their shame they have to harmonize subject with object. Lee sung boo makes subject into object by using intermediate, mountain. We can see the mountain as a intermediate in a collection of poems, Midnight Climbing. In this collection of poems the subject acquires his worth of existing, but we can not find insight of history which was a virtue of Lee’s early works. In Jiri Mountain the poet composes poems by writing about mountain which harmonize subject with object perfectly. In this collection no more exists the emotion of sorrow, and the collection recovers the role of consoling the grief of past mass. My major object of concern to Lee’s works was to classify them into some periods and specialize the relation among the periods. So this paper only contains the origination and changing of sorrow. This is the limit of this paper.