The article is a presentation of the subject of a lawyer in the Russian literature of two eras – the second half of the nineteenth century and the beginning of the twenty-first century. The object of comparative analysis are two literary texts: the first is the story by Leo Tolstoy – “Father Sergius” (1911), the second is a novel by the modern Russian writer – Evgeny Vodolazkin, which entitled “Laurus” (2012). The author of the article concludes that the multifariousness of the life of lawyers in both writers underlines their life experience on the way to holiness. An important element of the characters’ description is their sinfulness, in particular the fi ght against their own pride and human passion. In the case of Leo Tolstoy, the image of his literary right-wing was influenced by the writer’s views on the essence of holiness and the complex human-God relationship. In their portraits of heroes striving for spiritual perfection, both Tolstoy and Vodolazkin show a connection with the genre of hagiography.