Despite official disapproval, playwrights and their translators in Singapore use heterolingualism to establish a Singaporean identity. Kuo Pao Kun’s work shows us the “little man” and demonstrates that English is the language of power. Quah Sy Ren’s work explores the plight of the local Chinese-speaker, suggesting that Chinese-Singaporeans are more firmly anchored in their cultural identity. In Alfian Sa’at’s work the single heterolingual speaker is splintered into a variety of roles shaped by age, ethnicity, and gender, with heterolingualism being a mark of intergenerational and interracial tension. These three plays offer three solutions to the problem of forging a Singaporean identity: one based on Singlish, one based on Chinese, and one based on multilingualism and translation. They destabilize the notion of independent and self-sufficient languages, thereby challenging the notion of equivalence in translation.