Rituparno Ghosh’s cinematization of Unishe April (1994) and Dahan (1997) is a systemic triad interrogative feminist narrative of a case of sexual and non-sexual violence, the gendered spatial politics of Calcutta and the performativity of Bengali masculinity. The present study delves into the nuanced portrayal of the bhadralok masculinities in the cinematic texts of Rituparno Ghosh’s Unishe April (1994) and Dahan (1997). This research paper aims to articulate the relationship of Bengali bhadralok masculinity and the scattered hegemonies of socio-cultural structures of domination and patriarchal systems operating on multiple levels in the Bengali context. The bhadralok politics of the yesteryears was built on a collusion with the colonial system and espoused a broad spectrum of ideologies, including nationalism, liberalism, and humanism. Scholarly writings on Rituparno Ghosh have documented gender politics with an implicit focus on the feminine and queer subjectivity. The arguments of the present paper depart from the idea that masculinity is a genderless and a reified construct. Through a specific focus on masculinity and the masculine ideology’s nexus with gender social structuring, the present paper questions the invisibilization of masculine power, privilege, and performance. The bhadralok masculinity, though seemingly progressive and egalitarian, the embodiment preserves the patriarchal status quo of unequal gender relationships. Through an interrogation of the intersections of the changing bhadralok masculinities and its complex nexus with the changing social and cultural institutions across time and space, the study asserts that the cultured and sophisticated bhadralok gendered order is a failed political reconfiguration of masculinity.