Taking as case studies the development of Pop Architecture and Radical Architecture in Eastern Europe and Latin America during the 1960s and 1970s, this paper questions the possibility of producing a dialogic and horizontal art history that seeks to abandon the colonial and hierarchical Center/Periphery model. By taking as a starting point theoretical formulations by art historians and critics such as Partha Mitter and Piotr Piotrowski, the article focuses on the specificity of projects resulting from Eastern European and Latin American contexts marked by authoritarian rule. The article asks to what extent Oldenburg’s use of enlarged everyday objects in his Proposals for Monuments and Buildings could be associated with formally similar projects produced by East European and Latin American artists — Tadeusz Kantor, Milan Knížák, Luis Pazos, Marta Minujín and Milton Machado. The article discusses in particular the relationship between the formal language of architecture and its ideological, political and social connotations. It focuses especially on artistic production that entered in a critical dialogue with the concept of public monuments taking the form of enlarged everyday objects that conceptually and formally inverted the manipulative practices of the authorities in the Soviet bloc and in Latin America under civil-military dictatorships.