The present article examines the concept of human existence as Being-towards-death in Heidegger's philosophy and Tolstoy's novella, The Death of Ivan Ilyich. Death is one of those intersections where philosophy and literature meet. Milan Kundera suggests that many of the themes Heidegger articulates about human existence appeared centuries earlier in the works of great novelists.The central question of this study is: to what extent can Heidegger’s ontological understanding of death be applied to Tolstoy’s portrayal of death in The Death of Ivan Ilyich? Both Heidegger and Tolstoy approach human existence as Being-in-the-world and Being-with-others. This Heideggerian starting point, like that of novelists who focus on human beings in situ, contrasts sharply with the metaphysical tradition that begins with a transcendental, detached subject.Heidegger and Tolstoy argue that humanity's immersion in the world and others leads to an inauthentic self. Confrontation with death is the possibility that nullifies all the possibilities of inauthentic life. Death reveals to the individual that all the everyday norms and conventions of Das Man (the "They") abandon them in the experience of dying. While everyday communal life feigns that everything can be mediated or represented, the encounter with death discloses the irreducibly unmediated aspects of human existence.The relationship with death constitutes a “self-to-self” connection that cannot be reduced to a “self-to-others” relationship. Despite the similarities between Heidegger’s and Tolstoy’s views on death, there are significant points of divergence between the two, which this article explores in detail.