This article or essay deals with the specific features of Konstantin Leontiev’s critical study devoted to a comparative investigation of two great novels by Leo Tolstoy, War and Peace and Anna Karenina. Leontiev gives preference to Anna Karenina, asserting that the main drawback of War and Peace is in modernizing and excessively complicating the psychology of the characters by the author. Leontiev also traces in the epic novel a larger number of excessive naturalistic details. It is stated that the writer observes a kind of stylistic progress throughout Tolstoy’s creative career, from War and Peace to the more perfect Anna Karenina and then to the impeccable short stories for common people. However, as this article suggests, drawing on the example of Nikolay Strakhov’s analysis of War and Peace, different convincing evaluations of the evolution of Tolstoy’s creative path are also possible. It is emphasized that Tolstoy, while endowing his historical characters with contemporary psychological features, still succeeded in creating a convincing aesthetic illusion in his novel. An idea is also expressed that Leontiev, concentrating on the novels’ stylistic elements, neglects the moralistic tendency already sensible in Anna Karenina and drastically growing in subsequent works. The main significance of Leontiev’s critical masterpiece lies in his subtle psychological and aesthetic analysis of a whole number of previously unexplored nuances of the great works. His preferential choice of one of the novels, however, even if skillfully grounded, still appears purely subjective, based on personal feelings, which is eventually admitted by the writer himself declaring at the end that the rivalling works are equally outstanding.