According to Martin Heidegger's philosophy, Dasein goes through several stages in their quest for liberation from everydayness and towards "authenticity". His guide on this path involves confronting the Anxiety (Angst) arising from awareness of mortality, and the Determination (Entschlossenheit) to understand one's existential guilt in the face of death. Therefore, this essay aims to illuminate Dasein's journey towards authenticity, drawing from the perspective of "awareness of inevitable death" in Akira Kurosawa's "Ikiru" (Living) movie and Leo Tolstoy's "The Death of Ivan Ilyich" novella, among the most crucial aspects of Dasein's movement towards authenticity are existential "anxiety" and "resoluteness". Therefore, an effort is made to examine these two elements by searching for examples in the mentioned artistic works. It seems that the religious perspectives of Tolstoy, on one hand, and the existentialist viewpoint of Kurosawa, on the other, have led the protagonists of the two artworks to have different destinies, despite many similarities. This essay aims to answer the questions aims to explore how the existentialist perspective of Heidegger has been practically and authentically applied in these two artistic works? And what impact has the contrast between Tolstoy's religious beliefs and Kurosawa's humanistic perspective had on the authenticity of their characters in the story and movie? The analysis results of the two main characters demonstrate that one, Watanabe, reaches authenticity in the sense of Heidegger. Meanwhile, Ivan, influenced by Tolstoy’s religious perspective, ultimately achieves salvation and Christian forgiveness but does not possess Heideggerian authenticity. This research is descriptive-analytical, with a comparative approach and a phenomenological perspective.