This article is devoted to the study of ‘demolition’ (destruction) of monuments as a cultural phenomenon, which unexpectedly emerges in certain historical periods. Whereas for a long time it was believed that one of the main functions of culture is the preservation of material achievements and the conservation of memories of the past in monuments and other ‘memorial signs’, recent years have demonstrated that, occasionally, various nations undergo a ‘civilizational explosion’ as a result of which representatives of the nation feel a need for a radical change of the memory, prompting a rejection of the past that is expressed in the destruction (demolition) of monuments. The purpose of this article is to analyze the cultural semiotics of the destruction, their origins, and the results of these radical transformations of the signs of the memories of the past. These transformations in people’s cultural behavior are studied in global and local contexts. Considerable attention is paid to the semantics of the demolition of monuments in Kharkiv, the second largest city in Ukraine, in the context of the historical experience of this city in the nineteenth and twentieth centuries.