To delineate the line between values of idealism and materialism for human beings means to find out the sense of life. In this respect, two legendary literature works, namely Gilgamesh and The Death of Ivan Ilyich, are in the focus. The idea is that human nature is controversial in terms of securing the most significant rules to live. In other words, human beings become deceived every time they trap into a pit of fallacy. They try to run the gamut of life, but they do not beget sufficient ideas for it. Two main characters, Ivan Ilyich and Gilgamesh are struggling in their souls while trying to decide on the right way in life. Such general estimation of both should be separated by peculiarities in how they start-up and where their final breath takes place. Being excerpted from the ancient writing source, the story of Gilgamesh is a mystical epic with points on the struggle of divine and human parts in a man. Here the struggle between passions inside a man and his devotion in part of gorgeous nature is contradicted. It was done to provide the central part of the Epic of Gilgamesh with its most comprehensive outlook. There is a point in Gilgamesh’s reasoning of how to act in his struggle with Enkidu, his friend being half-wild. The main collision is represented when the protagonist thinks of whether he will go out of this situation as a winner or as a loser. In this respect, the death of Enkidu is considered as the “trophy”. At this point appears the pivotal inner redemption of Gilgamesh. He decides to reduce the feeling of rage against Enkidu. The support in overcoming human passions refers to the prayers of Gilgamesh to gods while stepping forward in his life journey. Gods help him stay on the right pathway, notwithstanding his outbursts to make a false step. Hence, a reader may suggest that different episodes and scenes prevailing in Gilgamesh relate to the dilemma of material and spiritual values. These significant features provide a choice that man should scope out. One should decide on whether to balance material and spiritual constituents by inner harmony or not. However, the last approach is too hard for any human being. Further still, the epic provides a theme on the immortality of Gilgamesh concerning Enkidu. It is even imposed in the idea that the protagonist is described as a half-god and a half-man. Moreover, Gilgamesh is a king. A good part of him that is concerned with a sound mind is related to gods and their will. In this respect, one should bear it in mind that a man is full of divine nature, notwithstanding strong passions. It is better to realize it each moment of life even if the hardest times happen. The tragedy of Ivan Illyich is discovered in his relationship to the circles of top-flight people who value the material “performance” of a man more than a man himself/herself. This main failure of the protagonist makes him devoted solely to material amenities. Being a judge, he used to have whatever he wanted in life. His disappointment in life and him, as an individual, emerged at the moment when he is taken ill. Starting with this part of the novel, Ivan Illyich is in terror of his final days. He goes insane about what he experiences. The end