The concept of ‘nostalgia’ has been recently coined to characterise the remnants of the Soviet past and its psychological impact in Cuban society. This article claims that during the 1960s, relationships with the USSR engendered divergent reactions, sometimes accompanied by strong resistance, to the canons of the ‘International communism’. The Cuban revolutionary experience did not always match with Moscow's priorities, especially in the cultural field, which was reflected on multiple debates about the appropriateness of applying the Soviet model. Although the 1970s and 1980s were decades of massive Soviet influences, producing in Cuba a growing adoption of the Socialist realism's techniques, the fall of the Berlin wall and the Periodo Especial have generated a renovated way of expression. Nowadays, a post-Soviet generation of artists seeks to unveil the fractures produced by the definitive collapse of the illusions embodied by the Soviet Union.