Modern Indian English drama has emerged as a significant literary space for interrogating questions of identity, selfhood, and socio-cultural transformation in postcolonial India. This chapter undertakes a comparative study of Girish Karnad and Mahesh Dattani, two of the most influential playwrights who negotiate the complex interface between tradition and modernity in Indian society. Through their dramatic representations, both playwrights foreground the identity crisis of individuals caught between inherited cultural frameworks and rapidly changing social realities. Girish Karnad’s plays draw extensively on myth, folklore, and history to explore the psychological fragmentation and moral dilemmas of modern subjects. Works such as Hayavadana, Naga-Mandala, and Tughlaq reveal how ancient narratives are reworked to question contemporary concerns related to selfhood, power, and cultural continuity. Karnad’s dramaturgy reflects the tension between collective cultural identity and individual desire, highlighting the struggle to reconcile tradition with modern sensibilities. In contrast, Mahesh Dattani situates his drama within urban, middle-class milieus, focusing on marginalized voices and silenced identities shaped by gender, sexuality, and family structures. Plays like Final Solutions, Tara, and Bravely Fought the Queen expose the psychological conflicts, emotional alienation, and social anxieties experienced by individuals negotiating modernity within rigid patriarchal and communal frameworks. Dattani’s theatre powerfully articulates resistance and self-assertion, especially through female and subaltern characters. By placing Karnad and Dattani in dialogue, this chapter demonstrates how Indian English drama evolves from mythic introspection to urban realism while consistently engaging with the question of identity. The comparative approach reveals that modernity in Indian theatre is not a rupture from tradition but a continuous negotiation, marked by conflict, adaptation, and redefinition of the self in a transforming society.