As one of the biggest names of european realism, Lev Nikolayevich Tolstoy has thoroughly described every characteristic of the Russian society in the nineteenth century. Out of many traditions, attitudes, beliefs and habits of people which the writers work has documented and thus immortalized, we have decided to dedicate this work to research of those cultural elements which are connected to death and dying, and to describe them parallelly and in light of writers personal life, religious beliefs and philosophical views. Starting from the assumption that the literature is one of the psychological mechanisms of dealing with death and dying, both of the writer and the reader himself, and considering that the literature reflects both conscious and subconscious thought processes in men, we hypothesized that Tolstoy's body of work would precisely demonstrate his attitudes towards death at each point of his life. As a sample for this analysis we have chosen four shorter novels (Childhood, Sevastopol in May, Three Deaths, The Death of Ivan Ilyich) which were written at the beginning, in the middle and at the end of Tolstoy's literal work. First, we have described the historical and the demographic situation of the Russian society in the time of writers life, and we have defined Tolstoy's place in the social context of the era. Then we have presented a short biography of author's life and went on with the analysis of the four short stories. The analysis has shown that some of the elements of the writer's style were present from the very beginning of his writing, and it traces the way these elements develop and combine with new ones over the years in order to compose the writer's final attitude towards death in the last period of life.