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The article is devoted to the comparative analysis of Esenin’s poetic self-portraits with his images in the lifetime portraits of I.G. Antropov and B.D. Grigoriev. When turning to the artistic world of Sergey Esenin and contemporary artists, the possibility of broad comparisons and identification of the typological kinship of the two spheres of art opens up. The representation of the author’s self remains one of the most important features of creativity, manifested both in lyrical poetry and in painting. Entering into a dialogue with the poet, the artist visualizes his idea of the portrait, responding to the lines that are consonant with him.