In Hong Kong, a postcolonial city, history writing has been under pressure from British colonial and Chinese nationalist discourses. In the past decades, Hong Kong cinema has used nostalgia to facilitate the writing of an alternative history. While narratives of official history are not neutral in terms of gender, some Hong Kong films exemplify how gendered memories interfere with the writing of history, such as Rouge (1987) which uses a prostitute to revisit the bygone days. In Wong Kar-wai’s cinematic past, women are often outside the social norm, such as the courtesan in The Hand (2004) and the prostitute and gambler in 2046 (2004). This article explores how these ‘indecent’ female figures are used to activate reflective nostalgia, question nationalist history, and construct ambivalent memories as well as postcolonial identities for the city. These films not only respond to the 1997 handover of Hong Kong, but also react to the political anxiety in the city in recent years. Despite its unique political background, Hong Kong cinema is paradigmatic in terms of the postcolonial culture it embodies. These films demonstrate that the writing of the past can be a culturally productive strategy against the twin forces of globalization and nationalism.