This dissertation deals with the concepts glasnost and perestroika during the Gorbachev era 1985–1991. It offers an explanation to the rise and fall of these concepts and casts light on their modern and postmodern implications, as well as their historical and generational preconditions. In light of the Soviet and Russian conceptual history, Gorbachev’s articulation of glasnost and perestroika is contrasted with the reception of these concepts in what at that time came to be called Russian postmodernism. Glasnost and perestroika both confirm and transcend Soviet modernity. They are both future-oriented but at the same time possess retrospective anchorage. The present study reconstructs the experience encapsulated in the concepts, the expectations they unleashed and the tensions they triggered. The Gorbachev era signaled a rupture in the temporal order of modernity. During this time Soviet modernity lost confidence in its self. With glasnost and perestroika a suppressed past opened up which blocked the futurist potential inherent in the present. The concept-theoretical perspective assumed in the dissertation helps explain essential aspects of the dramatic turn of events. Postmodernism’s relationship to the concepts is mainly antagonistic. At the same time glasnost and perestroika were essential to the self-identity creating process of postmodernism and its development of an understanding of a specific late Soviet postmodern situation. Beneath the surface a conflict evolves, constituted in intergenerational terms. The vast differences in deployment of the two key notions appear related to generation specific historical experiences. This is apparent in the glasnost- and perestroika discussions of the 19th and 20th centuries. In several respects the 20th century discourse reflects that of the 19th century. The analysis in the present dissertation demonstrates how Gorbachev, on the basis of his generation-specific experience as a man of the 1960s actively sought to articulate an alternative reconstruction (perestroika) and did so with a distinct ideological accent. The postmodernists, the last Soviet generation, bore the imprint of the stagnation of the Brezhnev era and had no ideal past to resuscitate. Instead of reconstructing social reality they tried to place themselves outside it. This apolitical stance however embodied both anti-political and political implications.