This essay deals with the holly fool (yurodivy) phenomenon in the cultural history of Russia providing interpretations of various texts – religious, medical, but primarily artistic ones (literature ...and film). Russian artists and intellectuals often practise mysticism and for them the sacred is a transcendental ontological reality to be experimented with. The author examines the way in which the yurodivy, an idiosyncrasy of Russian folk culture,at a certain historical moment became entwined with the thought of Russian authors such as Dostoevsky, Berdjajev and Tarkovsky, providing them with a form for a religious conception of art and a specific vision of the artist as a yurodivi “who mocks the world by day, only to mourn it by night” and artistic works as “pathways towards the other world”.