Authors have throughout history shown a tendency to revive the archetypal literary heroes Odysseus and Penelope. Homer constructed in his Odyssey a marital relationship which is based on mutual respect, understanding and love, while confirming family as the central social unit. The relationship between Odysseus and Penelope is therefore presented as the ideal human relationship, especially between a male and a female partner. The motif underwent major changes in different literary periods and acquired elements specific to each period, which is most visible in contemporary drama where it shows elements of Modernism and Postmodernism. None the less, the connection to war and post-war periods remains present. The aim of this work is to analyze contemporary European adaptations of the motif of Odysseus and Penelope in drama, while observing them through the matrix of most important values presented in the Odyssey and with respect to the ideas and principles that shaped the contemporary point of view. First and foremost this refers to the Psychoanalytic and Feminist theory. The analyses in question include ten different dramas, dating from the beginning of the 20th century until today, which affirms the topicality of the motif as well as its capacity for variation. Each of the included dramas enriched the European literature of the period it had emerged from and gave its special contribution to the overall motif. The analyses show a double tendency. In the first part of the 20th century, during the period of Modern literature, a span of dramas emerged that offered an interpretation from an exclusively male point of view, as a result of which Penelope became a secondary character or appeared only as a male construction of the female. The focus shifts drastically from Odysseus to Penelope in Postmodernist literature, as the authors try to emancipate their heroine showing her at least equal to, if not even more powerful than her male partner. In both cases one of the results of the motif’s adjustment to contemporary literature is that apart from Strauß’s Ithaka, all dramas fail to fulfil the mythological structure due to socially conditioned obstacles. Nevertheless, the significant number of existing dramas, as well as the manner in which they are shaped, prove that the motif is topical because it examines the elementary social relationship between a man and a woman, whether these poles are considered as psychological or biological categories. The motif proves adequate to be adapted to different settings, as well as to question diverse social norms.