This dissertation interrogates the intertextual and intercultural exchanges that, since the 19th century, have consistently led to the uniform, exoticized, and limiting literary and cinematic construction of the Roma as freedom-loving misunderstood outcasts with outstanding musical skills. The formation and reiteration of these images is presented as the result of four key political and cultural moments: the emergence of nationalism as an ideology in the 19th century; the genesis of the motion picture as a dominant medium in the early 20th century; the cultural and ideological East-West dichotomy created during the Cold War; and, finally, the rapid development of new media and technologies (DVD, Internet, etc.), as well as new modes of production and distribution related to the opening of inter-European borders in a post-Cold-War world context. A number of literary and cinematic texts that illustrate these representational shifts are examined in roughly chronological order. In the 19th century, Hugo's Notre-Dame de Paris, Mérimée's Carmen, and Pushkin's "The Gypsies" were critical to the establishment of the image of the "Gypsy" as a traveling dancer, and as part of an interethnic romantic triangle. This image was then visualized in early cinematic adaptations of these texts, particularly through interpretations of the "Gypsy" embodied by the Hollywood star system in the 1930s and 1940s, including performances by Rita Hayworth, Marlene Dietrich, and Orson Welles that set the tone for later portrayals. Although such performances and ideological constructs were denounced by Cold-War-era Communist ideology, they were nonetheless reproduced in Eastern European cinematic variants, and became particularly prominent in the late 1960s and early 1970s, as revealed in the work of Yugoslav (Petrovic, Paskaljevic) and Soviet (Loteanu, Blank) directors popular with East bloc audiences. In contemporary international cinema, French-Algerian-Romani director Tony Gatlif's and Bosnian-Serb Emir Kusturica's "Gypsy films" attempt a layered, multicultural approach to Romani representation, but fail to avoid earlier romanticized depictions of the ethnic group as carefree non-national musicians. The dissertation concludes by outlining the ways in which American, European, and even Asian cinematic and televisual texts continue to recycle 19 th century literary representations in current media narratives within a globalized culture.