This paper explores the myth of Chitrāngadā as reimagined across South Asian literary and cinematic landscapes – from the Mahabharata to Rabindranath Tagore’s dance-drama চিত্রাঙ্গদা (1905) and Rituparno Ghosh’s film Chitrangada: The Crowning Wish (2012) – to examine the performative politics of gender identity. Using Judith Butler’s framework of performativity and transformativity, the paper investigates how gender ambiguity and bodily transformation challenge heteronormative structures. Chitrāngadā’s depiction shifts from the epic’s gender-role transgression through Tagore’s theatrical exploration of transformation to Ghosh’s cinematic engagement with gender reassignment surgery. Central to this discussion is whether bodily transformation signifies heterosexual conformity or genuinely alters the queer psyche. The paper asserts that each reappropriation questions the stability of gender categories, revealing how both performative acts and bodily changes paradoxically destabilise rather than reinforce gender identity. By tracing this lineage from epic to screen, the paper demonstrates how cultural texts both uphold and challenge normative gender discourses, offering a South Asian perspective on the intricate relationship between body, performance, desire, and identity.