This dissertation examines Ukrainian painting of the perestroika era produced by the last generation of Soviet artists trained in the Socialist Realist method and steeped in the Manichean dualism of official and unofficial cultures. While rejecting the ideological purpose underlying their training, these Ukrainian artists witnessed not only the decomposition of Socialist Realism but also that of Soviet Socialist reality. I explore the historical circumstances during which this new art was born, displayed, and reviewed, particularly the semi-alternative exhibitions scene and the art squats illegally populated by artists in Kyiv and Moscow. Propelled by the paradoxical nature of perestroika, these artists were challenged to create a new quality in art while still invested in the past with its pre-existing art styles and specific expressions of local Ukrainian history--especially during the Baroque epoch. My analysis of major---but understudied---paintings utilizes archival materials, rare catalogues, and my interviews with numerous artists. I show that the hybrid nature of Ukrainian perestroika era painting reveals the porous nature of borders that separated East and West in the 1980s. My text shows how distant and sometimes distorted echoes of Western theoretical concepts, such as Postmodernism, Neo-Expressionism, Transavantgarde and Neo-Baroque, reached and impacted late Soviet art. These terms were freely employed by most sympathetic yet often disoriented liberal Soviet critics to describe the new phenomena. The artists themselves were not entirely familiar with the trends, yet they readily accepted---and then just as eagerly denounced---such definitions. My dissertation carefully tests and demonstrates the relevance of those theories to Ukrainian perestroika era art. My conclusions are based on a critical reexamination of Soviet era material, including the permutations of late Socialist Realist doctrine and the debates between Moscow Conceptualists and unofficial meta-realist poets.

Beginning with the uproar created by Arsen Savadov and Heorhiy Senchenko's scandalously popular Cleopatra's Sorrow (1987), shown at the 1987 Youth Exhibition in Moscow, and continuing with the relocation to the Furmanny Lane art squat of the Resolute Edge of National Post-Eclecticism group, perestroika era Ukrainian painting appears irrevocably entangled with the culture of Moscow during the collapse of the USSR. I show how Ukrainian artists maintained throughout a productive dialogue with Moscow Conceptualism. Highlighting the constellation of often conflicting concepts and ideas that define and inform this generation's art, my dissertation rejects singular definitions attributed to it. I argue instead that the plurality of cultural impacts and discoveries of local histories require a more nuanced explanation, and my findings indicate that the state of political turmoil of the time is, in fact, reflected in art that subscribed to partial explanations and fragments of multiple discursive systems.