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The article offers an analysis of Russian and foreign films shown at the 2022 “Artdocfest” documentary film festival. The focus is on the films, on the one hand, united by the theme of visual and performative arts; however, on the other hand, the author concentrates on how directors raise problems related to Russian society and the country in general and try to solve them. Evgeny Mitta’s work Pepperstein, Surreality Show (2021, Russia) analyses the techniques of portrait film and dramaturgy that made it possible to bring the viewer to philosophical generalizations, reflections on strategies for educating generations in the USSR/Russia and the ways of transferring the cultural capital of the Sixtiers. Maria Novikova’s film Artists of Perestroika (Netherlands, 2021) describes the cultural space of the 1980s and the life of the characters of the 1980s artistic avant-garde thirty years later. The article focuses on the film The Cars We Drove into Capitalism (2021, European coproduction) by Boris Missirkov and Georgi Bogdanov, in which, using the example of the history of the East European automobile industry, the directors offer the viewer a social drama about the end of the socialist era.