In times of crises and existential disorientation, the arts often lean on gestures of radical doubt, the articulation of which demands the art of masquerade, deception, diversion and dissimulation, and simultaneously includes characteristic constellations of pathos and melancholy. The authors of this article analyse different artistic projects in Slovenia, Germany, Russia and elsewhere, which were created in the breakthrough period after the fall of the Berlin Wall and connect these projects to the wider social events of the previous two decades. In their treatment of the contemporary ‘art of doubt’ they focus especially on the perspective of the political and existential and in addition point out the fundamental historical concepts of doubt which have influenced the development of theatre and experimental knowledge in Europe from the beginnings of the early modern era until today.