The crossword, one of the notable phenomena of post-Soviet Russian culture, still remains largerly unnoticed by researchers. In this paper, we attempt to show the heuristic potential of the crossword as material for study of post-Soviet society. Proceeding from an interpretation offered by O. Shevchenko in his articles, the author proposes emphasizing the significance of studies in traditional culture and cognitive psychology when seeking to understand the nature of the crossword as a specific cultural phenomenon. Shevchenko has noted an increase in the consumption of crosswords in the 1990–2000s. She explains it by noting the special significance of puzzles to which an intellectual aura attached for the post-Soviet intelligentsia. In this paper an alternative view of crosswords is proposed. The crossword not only became more popular, but also was simplified. The transformed form became incorporated into the social and cultural context alongside phenomena of folklore. The crossword literally starts to perform functions similar to those carried out by riddles. Having appeared as an agent of transmission of uncritically accepted, “encyclopedic” knowledge, the crossword becomes a medium of transmission of everyday experience; it also naturally reflects and translates the norms and values of the community in which it appears. The author supports her conclusions by utilizing the results of research in other fields, that in one way or another are connected with crosswords. Acknowledgements. This paper was prepared as part of the project of the academic research group № 17–05–0003 within the scope of the “HSE Academic Fund Programme” in 2018 and within the scope of government support of the leading universities of Russian Federation “5-100”.I am very grateful to my scientific supervisor B. E. Stepanov, who put so much effort in supporting this study and encouraged me never to give up. I also want to thank the wonderful N. V. Samutina for help in editing and composing the article.