Roman Polanski's Death and the Maiden (1994), the adaptation of a play written by Ariel Dorfman, can be interpreted on various levels. Although not stated explicitly, it is unambiguous that the background of the story is the Chilean dictatorship of Augusto Pinochet, though it could equally have been any East-Central European or Latin American country with a dictatorial past. This motion picture raises questions concerning human consciousness, guilt, pain and torture (both emotional and physical), revenge and moral uncertainty. Three episodes of Polanski's life may add a special significance to this adaptation. Being a Holocaust survivor, the Polish director experienced the repression of a dictatorship and the effects of human cruelty. Furthermore, his pregnant wife was brutally murdered by the Manson Family. Also, taking into consideration that he was found guilty of unlawful sex with a minor, he knows how society and individuals punish someone for his or her crimes. The aim of my article is to examine the possible interpretations of the movie, paying special attention to Polanski's approach towards tragedies, dictatorships (in both East-Central Europe and Latin America), and personal guilt, and also to highlight what message the film may transmit to future generations.