One of the most provocative current contributions to think through possibilities of understanding media is a study Towards Evil Media Studies, 2007, written by Matthew Fuller and Andrew Goffey and their subsequent book Evil media, 2012. The authors are inspired by a controversial legacy of Niccolo Machiavelli, Baltasar Gracian and especially Arthur Schopenhauer and his Eristic Dialectic: the Art of Being Right (1830–1831). There is a whole network of complex and unnoticed relationships among programmed media and their users. Fuller and Goffey lead us to imagine this environment as a gray zone that provides space for manipulation. The lecture presents the history of the metaphor of gray zone as well as examples of grayness and evil in contemporary social media.