Prohibited jokes secretly told in the Soviet block were a delegitimizing factor that unleashed a liberating laughter, which revealed the contradictions and the gap between propaganda and reality. Considered grounds for persecution in classic Greece or a “counter-revolutionary activity” in the Soviet Union, jokes and humor are analyzed by the author in an attempt to show the various theoretical approaches from ancient times to the 20th century. He further analyzes the clandestine role of political humor, a hazard and challenge to the status quo. The author also differentiates the periods of “Communist” political humor, from the Russian Revolution to Gorbachov, with a compilation of all “actually existing socialisms” in Europe. Lastly, he enquire the crisis of socialist values and the disruption of legitimacy through jokes.