The article is devoted to the phenomenon of “desacralizing” biography at the example of several studies of A.P. Chekhov’s life and works, and to the reasons of popularity of such biographies among the mass readers. This way to describe Chekhov’s life is partly connected with the memoir tradition, in particular, with the essay by N.M. Yezhov “Anton Pavlovich Chekhov (An attempt of characteristics)” (1909). N.M. Yezhov tried to create an objective yet creative psychological portrait of the writer, based on the experience of personal communication with A.P. Chekhov. The attempt was reduced to a many unprovable invectives and was perceived by the majority of contemporaries with a lot of skepticism. Today this genre of Chekhovian studies and literary criticism can be considered as an example of a postmodern approach to culture, which is characterized by de-canonizing of studies and depiction of classical cultural heritage. A book, which demonstrates all peculiar treats of the postmodern “desacralizing” way of cultural research, is the book written by D. Rayfield “Anton Chekhov: a life”. On the example of D. Rayfield’s book, we can see all the specific features of the phenomenon of “warts-and-all biography” (as the author describes the essence of this approach in one of his interviews): polemical references to the Chekhovian studies researches, quasi-scientific way of the presentation of the facts, the illusion of an objective presentation, combination of proven facts with the biographer’s unprovable assumptions. A careful analysis of all the components of desacralizing biographies allows us to conclude that the main target audience of their creators is the popular readers, which perceive de-canonizing works (pretending to be academic books) as a fully scientific evidence-based new look at certain aspects of Chekhov’s biography. In D. Rayfield’s work, this impression is also formed by the purposeful transformation of some ordinary facts of Chekhov’s biography into the crucial events in the writer’s life. The study of such works and the reaction of the wide readers to them is necessary for academic science to approach theoretically the contemporary cultural trends.