The present essay is devoted to the various manifestations of transformation in Slavic literatures after 1989, when 300 million Slavs found themselves in the cultural paradigm diametrically opposed to the communist one, but not quite what it was designed to be by the dissidents and opposition members, i.e. advocates of civil society. This comparative panorama of Slavic literatures is presented from the perspective of postmodern culture and philosophy (Lyotard, Bauman, Rorty, Prigogine, Foucault, Derrida among others), legitimizing with its theories pluralism, the understanding of the multi-meaning nature of truth, the polyphony of cultures, and the significance of all minorities for the spiritual development of humankind. On the basis of selected examples from the literatures of West-, East- and South-Slavic countries, the author attempts to identify the crucial elements of transformation of the social and literary self-awareness of different generations in the post-communist Slavic countries over the last fifteen years. In the works of J. Topol, V. Pelevin, T. Rżewicz, D. Ugresić, T. Zabuzhko, or D. Bieńkowski she seeks an answer to the question what was realized out of various dreams of a better and braver world of pluralism and democracy. How do the transformationers, the transformed and the self-transforming “inhabitants” of the new reality recognize their social and ethical situation? Who are, in light of literature, the heroes of our time, and what is behind the notion of “new sensitivity”? What does the so-called “realcap” (real capitalism) mean in literature? And also, which spaces of freedom does the democratic system open for writers and minorities, and which new worlds of imagination does it create in a search for metaphysical, mythical, thanatological, religious and esoteric dimensions of human existence, constrained in the past by imposed, top-down atheism.