ABSTRACT While Arun Kolatkar’s modernist and experimental modes have received critical attention, his application of irony remains under-researched. This article argues that his playful and ironic registers are a form of experimental modernism, employed to address socio-historical phenomena in South Asia. The self-aware irony in Kolatkar’s early work anticipates the use of personae in his later works. His poetry assumes the postcolonial stance of empowering the tyrannized. He ironizes from the perspective of the feminine and non-human to assess foundational myths and 20th-century events in India. As an ironist, Kolatkar acknowledges the speaker’s authoritative position in the text and strives to diminish hierarchies between the ironist and subject. Through textual analysis of the poet’s works, this article demonstrates that the purpose of Kolatkar’s critique and his attention to landscape is to challenge divisive and conservative ideologies that perpetuate conflict and to foreground the resilience of individuals in South Asia.