This chapter is a comprehensive introduction to the precariousness of Sri Lanka’s present as it is characterized by the legacy of the civil war, Sinhalese ideas of supremacy, a unique kind of nationalist and militant Buddhism, highly ideologized political parties, a dynastic political culture, the breakdown of its economy, a growing dependency on countries like China, India and the US, the ousting of its former Prime Minister and former President, and the recent election of Anura Kumara Dissanayake (NPP) as new President. First, this contribution asks why Sri Lanka failed to create an inclusive nation-state and what can be learned from its relative failure in dealing with difference and diversity, religions and ethnicities, traditions and histories as well as memory, ideology and political doctrines in the context of its highly traditional, stratified and divided society. Secondly, it is argued that one way out of this conundrum is to take a look at a sphere where creative thinking is possibly endangered but not strictly censored, i.e. Sri Lanka’s vibrant art scene, and to explore how concepts of community, of living together, of building ‘the new country’ (Sundarji) are envisaged in its literary and theatrical production, in cinema, the performing and visual arts. This engenders an analytical perspective which — though it takes the past into account — primarily looks toward alternatives and possible futures as articulated in the cultural imaginary.