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Iranian cinema underwent a significant transformation in the late 1990s concerning the presence and primacy of women and their issues in films. However, it would be an oversimplification to label these films as uniform in their concerns. This study selects three films – The Circle (2000), Boutique (2004) and I (2016) – as case studies, focusing on the plight, constraints and responses of Iranian women in the masculine spaces of Tehran. The Circle, with a defeatist attitude, portrays Iranian women as passive victims trapped in a web of gender-based societal oppression. Boutique tells the story of a young woman resisting constraints and societal judgements in her pursuit of independence but fails to validate the legitimacy of her actions. I features a strong, independent female protagonist who successfully challenges patriarchal norms and conventions. In doing so, she becomes a paranoid outcast, treated by society as a criminal. This study emphasizes the interrelations among these three films and their differences, particularly in the films’ treatment of women’s situations and their respective stances. The article aims to provide a deeper perspective on the cinematic representations of the relationship between Iranian women and urban spaces.