The paper addresses the thematic intersections in the works by Y.K. Olesha and V.M. Shukshin, which are of interest as sources of understanding the specifics of the writers' poetics. The relevance of the study is due to the need to explore this problematic dialogue in order to adequately perceive the cultural, historical, social, and everyday aspects of the literary texts that reflect different periods of the literary process. A number of methods and techniques have been applied, including description and synthesis, cultural commentary, and philological analysis. Olesha entered literature as a European writer, while Shukshin, on the contrary, is considered a researcher of the Russian national character. So similar images and situations (love triangle, technology, the material world, circus, culture–civilization opposition, etc.) attract the readers’ attention as revealing the author's attitude to creativity and understanding of his tasks in art. The conclusions concern the peculiarities of Shukshin's dialogue with his predecessor, as well as the specifics of symbolic gestures in the two writers’ everyday behaviour and the writers’ worldview in different historical epochs of the Soviet era.