In this paper, a philosophical analysis of the concept of "toska" in Russian literature and cinema is carried out. The research is carried out to a greater extent based on the concepts of Russian existentialist philosophers who analyzed the meaning of toska, despair, sadness and boredom. The research is based on the literary works of F. M. Dostoevsky, L. N. Tolstoy and A. P. Platonov, as well as films by Andrei Tarkovsky, Alexei Balabanov and Alexander Fedulov. It is important to point out the conceptual difference between toska and the other concepts given, thereby refuting the thesis about the understanding of toska as a negative feeling of uncertainty associated with a sense of deep loss, having a strict reason. Therefore, in this study, by pointing to the temporal division of toska, deducing it as toska-to-the-present (reflected in the ideas of F. M. Dostoevsky), toska-to-the-past (the concept of longing in the "Notes of a Madman" by L. N. Tolstoy) and toska-to-the-future (in the works of A. P. Platonov), it is indicated that toska can be understood as something unethical, prompting in the subject the desire to enter the transcendent, the search for sacred meaning.