Drama in Indian English has become a place whereby key negotiations among culture, identity and modernity are played out and fought. Among this changing topography, the works of Asif Currimbhoy and Mahesh Dattani can be seen as a sensitive and critical approach towards the changing curves of Indian postcolonial subjectivity. This paper is a cultural studies approach that explores the complexity of cultural hybridity and identity formation, gender politics and enduring contradictions between tradition and modernity, within the plays of these dramaturgs. Based on the theoretical concepts of Homi K. Bhabha, Stuart Hall, Raymond Williams and Judith Butler, the paper will discuss how the plays of Currimbhoy express the anxieties and ideological discontinuities of post-independent India and how it experiences the tensions of the clinging colonial legacies, nation-building, and defining its identity. On the other hand, the theatrical vision of Mahesh Dattani indicates the fractured and, in many cases, ambivalent identities informed by the elements of the globalization and post-liberalisation urban space. His depiction of such problems as sexuality, family crisis and marginalisation, as well as social hypocrisy, emphasises the multifacetedness of the modern Indian identity. Comparing the two dramatists, this paper has shown how Indian modernity is being constantly renegotiated by discourses of competing nationality, gendered, class, and sexuality. This interdisciplinary approach of this work supports the topicality of cultural studies in the process of interpreting the performative manifestation of changing social realities. Finally, the paper suggests that Currimbhoy and Dattani bring an important contribution to the comprehension of the cultural negotiations upon which Indian English drama and the overall story of sociocultural transformation in India are constructed.