South Africa and Russia achieved two of the most remarkable political transformations in modern history, yet significant numbers of their citizens feel a longing for aspects of the old regimes. While there have been some studies of nostalgia among older Russians and South Africans, the following is the first comparative qualitative examination of the phenomenon among young members of the countries’ inaugural “born free” generations: those who came into the world just before or after the fall of Apartheid and Communism, and have had little or no experience of life prior to regime change. Its purpose is to examine how and why young people growing up in post-authoritarian transition societies experience, and long for, the past. I conducted in-depth, semi-structured interviews with seven South African and five Russian youths, recruited through purposive sampling, who reflected on the ways in which the recent past impacts their lives, self-perceptions and socio-political identities. While they differed in some areas, respondents from both countries identified several broadly shared areas of nostalgia, clustering around a perceived loss of community, moral values, personal safety and social trust; and a concomitant rise in individualism, materialism and anomie. Employing a Marxian engagement with symbolic interactionism and interpretative phenomenological analysis, I analyse their transcribed testimonies in light of the relevant scholarship on nostalgia, social memory and transition studies, alongside theories of post-modernity and critical sociology. I conclude that their nostalgia may be the product of Russia and South Africa’s belated and compressed transition from “modern” to “post-modern” societies; a rebellion against the harsh transition to a Baumanian “liquid” life characterised by economic precariousness and the fraying of social bonds; and/or an expression of profound ambivalence that struggles to reconcile nostalgic regrets about the risks and human costs of globalised capitalist polyarchy, with a hunger to exploit the freedom and opportunities it offers. / Theses (M.Soc.Sc.)-University of KwaZulu-Natal, Durban, 2012.