In postcolonial Southeast Asia, contemporary theatre artists have repeatedly contested national imaginings of democratic identity, particularly in the second half of the 20th century when nation-building was pivotal to cultural production. Often influenced by avant-garde theatre in the West, particularly from the 1950s and 1960s, these artists envisioned worlds where difficult issues could be openly deliberated, using contextually grounded performance texts and vocabularies to express the tensions of being modern, plural, and different. As state-led notions of national identity remain largely stipulated and singular, artists who continue to experiment with decentered and multi-perspectival frames take on resistance to the hegemony. Difference and disagreement with the state are regarded as detrimental to national unity, and thus theatre that advocates criticality can be deemed disruptive. Artists who nonetheless adopt these approaches to theatre take on roles of alternative leadership, in which their vision and pioneering work towards radical change becomes influential in transforming the socio-political and cultural landscape. This chapter explores how three Singapore theatre practitioners, Kuo Pao Kun, Ong Keng Sen, and Kok Heng Leun, have made choices that question the policies and practices of the state, yet in so doing generated valuable platforms for deepening connections with the political.