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Abstract: The article is devoted Zabolockij’s poem «Portrait» (1953). Several important contexts associated with the biography of the author, and the biography of the artist F. S. Rokotoff and his model A. P. Strujskaya. There is recreates the philosophical (G. S. Skovoroda, N. F. Fedorov) and aesthetic (A. A. Sidorov and critics circle GAKhN) context of the poem. As the main source of literary there are offered two poems of forgotten poet A. F. Meissner. Undertaken analysis allows to argue the idea that poetry and poetics of the late Zabolockij not easier, but more difficult than his early poems. Understanding non-obvious meanings, analysis and interpretation of Zabolockij’s poems 1950s require recreating both near and distant cultural contexts.