Both nostalgia and melancholia have been portrayed as psychological inabilities or refusals to mourn, coming to denote a common failure to having adapted to situations of social and political change. Both concepts have been used to either condemn the conditions they diagnose, or, alternatively, to hail them for their emancipatory potential. In this regard, both nostalgia and melancholia have been used effectively, separately and alongside one another, as instruments for political critique. However, with this mutual opposition to mourning, melancholia and nostalgia have also been used in ways that make them almost interchangeable. In the absence of a detailed and direct comparison of these two concepts, this article explores the differences and overlaps between melancholia and nostalgia, as well as the different kinds of analyses of posttransition societies they enable. This is achieved through the juxtaposition of a particular regularity in post-apartheid South African popular culture, Afrikaner self-parody, which is characterized as melancholic, with what has frequently been called Ostalgie, nostalgia for the former German Democratic Republic.