Immediately after the occupation of Czechoslovakia by the troops of the Warsaw Pact in August 1968, artists, writers, and philosophers began to suffer from various forms of physical, psychological, symbolic and legal exclusion. This was also implicitly an exclusion from the normative sphere of public life, which was strictly controlled by the repressive official political apparatus. Starting from a thorough examination of some selected case studies – for instance, a close reading of Jan Patočka’s Charta 77 text The Obligation to Resist Injustice –, the paper seeks to investigate the question of how far “non-conformist” Czechoslovak art and philosophy were perceived as transformative and disruptive practices. This question, which remains significant to the present day, raises a host of other questions: How is the relation of dis/order and responsibility to be evaluated? What changes does the experience of exclusion and (internal and external) migration bring with it for the practice of philosophy and the freedom of art? And not least, how far is our understanding of these positions still dominated by a reductionist perspective on “the Eastern Bloc”? As we shall see, a critical analysis of these issues might help to reflect on linguistic, epistemic as well as political hegemonies, to revisit the still rather one-dimensional Western (art) history of (post-)modernism, and thus to question and reframe holistic historiographic and theoretical narratives.