The essay provides a brief overview of the changing literary critical definitions and cultural evaluation of fairy tales. I argue that the most remarkable feature of this heterogeneous textual corpus resides in the affective narratological potential to stimulate wonder, to activate the imaginative aspect of the mind. The fantastic vision of a fictional alternate universe enchants readers by suspending the natural physical laws and rational logic of ordinary consensus reality. But it also provides pragmatic assistance in understanding the perplexing complexity of human existence and the diverse thought systems attempting to make sense of it. Postmillennial transmediation tendencies expand the fairy-tale web with a dizzying variety of new forms, yet the genre’s traditional merits prevail in the celebration of empathy, solidarity, social justice, and a relentless optimism against all odds.