The chapter seeks to uncover how Estonia after the 1990s defines itself through films, contemporary art and the Song and Dance Festival. I par- ticularly focus on these three spheres of national cultural production as containing different but meaningful narratives of Estonianness, created within society and by discourses that are both hegemonic and critical. Arguably, none of the areas is homogeneous, and they have been trans- formed in the past two decades. What is more or less common in these understandings of the nature of Estonian nationalism is the grounding in the experience of “triple colonisation” (Baltic German, Tsarist Russian, and Soviet) (Peiker 2016, 114). It is a variety of interpretations of the Soviet past that continues to be an unalterable “stumbling stone” for both hegemonic and critical discourses, uncovering their inner ruptures and challenging their consistency.