The article examines typological intersections between the early works of Leo Tolstoy and the works of the 1850s of Egor Kovalevsky. The theme “Egor Kovalevsky and Leo Tolstoy” has not been studied comprehensively and systematically in Russian literary criticism. The research develops from the history of personal relationships between the writers during the Danube Campaign and the Sevastopol events to a comparative study of the writers’ works created during the Crimean Campaign. Tolstoy’s “Sevastopol in December” and in Kovalevsky’s “The Bombing of Sevastopol” reflected the similarities in the authors’ concepts, themes and images. The article justifies that the central theme developed in the writers’ oeuvre was a person and their role in history. Similarities and differences in the portrayal of the heroic events of the defense of Sevastopol by the writers are considered. Kovalevsky’s essay and Tolstoy’s first story are closely linked by one idea – the sense of civic exaltation, national identity. In describing the Russian soldier, his character, the heroism of the defenders of Sevastopol, the writers follow the “truth of life”. Kovalevsky captures the names of the direct participants in the war. With one detail or episode of the last minutes of their lives, Kovalevsky draws the reader’s attention to the “ordinary heroes” of Sevastopol, emphasizing the importance of their individual feat. Tolstoy’s heroes, on the contrary, are nameless: it is the general mood of the defenders of Sevastopol that is important for the writer. There are common features in the narrative manner of the two writers: ways of depicting heroes, accuracy and imagery of landscape sketches. A few strokes and precise details convey the state of Sevastopol. The mood associated with the state of the city is emphasized by the details of the landscape. The similarity in describing the heroes’ and the narrator’s psychology is expressed through the image of fog. The features of the authors’ creative manner and the role of the narrator are analyzed. There is an obvious difference in the creative methods of Kovalevsky and Tolstoy. Describing real details with historical accuracy, Kovalevsky paints a romantic picture with bright “strokes”. Kovalevsky uses concrete real details most often as a way to emphasize a bright feature he has noted in life, while Tolstoy seeks to show (highlight) the quality of life rather than its specific feature. The difference between Kovalevsky’s essay and Tolstoy’s story is also in the assessment of the historical event. Describing the bombing of Sevastopol as a historian, Kovalevsky does not abandon moral and political generalizations. Thus, the manner of narration and the ways of depicting heroes testify that both Tolstoy and Kovalevsky solve one problem with different artistic means – to truthfully portray the reality and the person as the “center of history”. In search of a true depiction of Sevastopol, Kovalevsky, a historian and romantic writer, moved towards realism embodied in Leo Tolstoy’s story.