The authors refer the issue of definition of contemporaneity as cultural and historical totality basing on the research results of a well-known theorist Boris Groys. Analyzing the progress of his ideas, the authors conclude, that the philosopher’s considerable contribution to the science is composed of the next phase of the development of the thesis about the art language as the base of contemporaneity construction and of the “natural selection” of contemporary art structures. The latter is not simply reduced to the postmodern “polylogue” variant, but implies a kind of contemporaneity patterns niche and “stabilization”. The patterns naturally tend to become complementary due to simple juxtaposition/ overlay in general time context. According to the authors, this circumstance does not prevent them from being turned by different political forces into locally dominating contemporaneity patterns (as in the case of Gesamkunstwerk Stalin). Contemporary art provides simple experience, that helps to retain the illusion of single and seemingly total contemporaneity. B. Groys leads us to the thought that art provides conditions for generating a significant reflective distance in relation to different social and historical situations. The distance gives an artist the opportunity to consider the reality comprehensively, given the autonomy, through the art language. However, we believe, that the most important philosopher’s achievement is not only drawing parallels between cultural and social and historical processes, based on the concept of art strategies influencing the social dynamics. He also managed to approach one of the most significant issues in culture theory and history – the opportunity to define contemporaneity as cultural and historical totality. According to his modernity theory, the origin of contemporaneity is hidden in the avant-garde art manifestation. He interprets the utopic by its nature modernist discourse, applied in art practice, through Nietzscheian will to power as redefining the new age philosophy. This article aims to analyze the progress of the issue of contemporaneity in the works of B. Groys and to explicate the complexity of considering contemporaneity as cultural and historical totality. The authors believe that the thorough study of the phenomenon of total artwork (Gesamtkunstwerk) as a soviet Stalin project and critics’ opinion analysis helps to create arguments limiting the opportunity of considering contemporaneity as totality.