Bimal Roy, one of India’s greatest filmmakers, gained international recognition forDo BighaZameen (Two Acres of Land, 1953), which became one of the first films to usher in the neo-realist movement in India.Many of Roy’s films were female-centric in a time when women were still fighting for their rights in post-independence India. Women in Roy’s movies have different identities, and while some represent ideal lovers (in films such as Parineeta and Madhumati), some are defiant of a normal social setup, representing different ideas and attitudes in traditional society. Three such women are Parbati and Chandramukhi from Devdas (1955), and Kalyani from Bandini(1963).These women not only question societal norms by their defiance, but also embrace their difference in society. While Paro indulges in spiritual love, though bound by her worldly marriage, Chandramukhi renounces the material world in search of devotional love. Kalyani on the other hand questions marriage and women’s societal roles, yearning for literal and figurative freedom. This paper focuses on three such women from Roy’sDevdas (1955) and Bandini (1963). Using semiotic tools, including music, dialogue, cinematography and characterisation, the paper studies the representation of women in Bimal Roy’s films while paying particular attention to the women who seek devotional love as opposed to material love and also question their marriages and social imprisonment.