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During the Yugoslav wars of the 1990s, Serbia fought to preserve a unified Yugoslavia, as its preservation also could have maintained the primacy of Serbian identity in place since the creation of the first Yugoslavia. Serbian identity had been inextricably linked to Yugoslavia, for Serbs comprised the federation’s dominant nation, culture, and language. Yet with each cease-fire at the end of each secession war, the importance of Serbian cultural products diminished along with the conflation of Serb and Yugoslav. The NATO bombing in 1999 solidified the sense of Serbia’s demise, and proved Serbian political and cultural insignificance. This revolutionary change in the Serbian nation, both in the country and its people, was not greeted with jubilation as in other Eastern Bloc countries. Serbia did not want independence; however, it was the inevitable outcome of the fracturing of Yugoslavia and its people into distinct nations with culturally exclusive expressions of identity. The tendency to characterize Serbia’s transition from Socialist to post-Socialist nation as exceptional is common. However, much of the academic literature focuses on the nature of the transition of ex-Eastern Bloc nations into respectable and recognizable democratic states, based on Western standards. Therefore, Yugoslavia’s wars are viewed as extreme anomalies, incompatible with the trajectories of other countries’ successful transition to democracy. Thus, Serbia was viewed as particularly backward; not only was it seemingly incapable of conforming to the Western norm, its people, and politicians were supportive of recalcitrant policies that isolated Serbia, virtually bereft of regional and international support, except from Russia, whose stances were nuanced and culturally loaded. This dissertation offers perspectives on Serbia’s transition to post-Communist, and draws from post-Socialist scholarship on Eastern Europe as a basis for understanding. In this way, this dissertation departs from conventional post-Communist scholarship on contemporary Serbia, and is engaged in a dialogue on Serbia’s political, cultural, historical, and social components of Serbia’s transition. This dissertation argues that Serbia’s transition to democracy bears little resemblance or relation to that of the other nations. As proof, I use historical events and literature on internal colonization to illustrate how Serbia’s position of privilege in Yugoslavia set a dangerous paradigm for sustaining Serbian hegemony and dominance. I contrast Serbia’s elevated position in Yugoslavia to its insignificance today, both regionally and internationally.In order to provide the cultural context for this contemporary reality of Serbia, I analyze the rifts in society between particular imaginings of the ideal direction for Serbia, as a preference of either Local or Western paradigms. These contrasting standpoints on Serbia’s cultural and political future materializes primarily through generational differences, whereby the Local is championed by artists and writers of the older generation, or the Yugoslav generation, whereas the West garners support from the younger generation, or the Serbian generation.