This article explores how European civilization' was imagined on the margins of Europe in the first half of the twentieth century, and how Balkan intellectuals saw their own societies' place in it in the context of interwar crises and World War II occupation. It traces the interwar development and wartime transformation of the intellectual debates regarding the modernization of Serbia/Yugoslavia, the role of the Balkans in the broader European culture, and the most appropriate path to becoming a member of the European family of nations'. In the first half of the article, I focus on the interwar Serbian intelligentsia, and their discussions of various forms of international cultural, political and civilizational links and settings. These discussions centrally addressed the issue of Yugoslavia's (and Serbia's) Europeanness' and cultural identity in the context of the East-West symbolic and the state's complex cultural-historical legacies. Such debates demonstrated how frustrating the goal of Westernization and Europeanization turned out to be for Serbian intellectuals. After exploring the conundrums and seemingly insoluble contradictions of interwar modernization/Europeanization discussions, the article then goes on to analyse the dramatic changes in such intellectual outlooks after 1941, asking how Europe and European cultural/political integration were imagined in occupied Serbia, and whether the realities of the occupation could accommodate these earlier debates. Serbia can provide an excellent case study for exploring how the brutal Nazi occupation policies affected collaborationist governments, and how the latter tried to make sense of their troubled inclusion in the racial ideology of the New European Order under the German leadership. Was Germany's propaganda regarding European camaraderie taken seriously by any of the local actors? What did the Third Reich's dubious internationalism mean in the east and south-east of Europe, and did it have anything to offer to the intelligentsia as well as the population at large?