Abstract: This article is dedicated to the two prominent figures in the art world of 1950’s-1960’s – abstract expressionist, representative of “painting of action” Jackson Pollock, and future generation painter, founder of the “environment” Allan Kaprow. On the grounds that the turn of the 1950’s-1960’s is viewed as a breakthrough era for the art of modernism, the article analyzes the artistic techniques of Pollock and Kaprow, as well as the social aspect of their work for determining the points of convergence and divergence in their practice. Critical and theoretical texts used in the article include the works of Clement Greenberg, Michael Fried, Yve-Alain Bois, and Allan Kaprow himself, who is known not only as a painter, but also as theoretician of the new artistic practices of 1960’s – assemblage, environment and happening. The focus of author’s attention became the insufficiently studied and untranslated into the Russian language text of Allan Kaprow “Legacy of Jackson Pollock” (1958), which defines the scientific novelty of this research. Within the framework of modernistic discourse, the works of Jackson Pollock are viewed as a pinnacle of “self-purification” of the avant-garde painting and realization of the principle of medium-specificity. However, some aspects played a significant role for artistic practices of the 1960’s, longing to cut ties with abstract expressionism. Reference to such aspects – performativity of Pollock’s painting, his representation on the graphic form, format and spatial dimension of his canvasses – allows determining continuity between the opposing trends of art of the 1950’s-1960’s, and reveal the role of Jackson Pollock as a crucial transitional figure at the turning point of modernism.