This doctoral dissertation is a study of three works: Marcela Serrano’s novel We Who Love Us So Much (1992), Ariel Dorfman’s play Death and the Maiden (1992) and its filmic version directed by Roman Polanski, and the documentary directed by Maria Elena Wood, The General’s Daughter (2006). Through the representations of subjectivist female characters in the works, we analyze what we call the vicissitudes of female identity in relation to the agitated sociopolitical circumstances that Chile lived from the sixties to 2006. In those decades, we observe the process of the construction of a revolutionary identity that culminates with the election of the Popular Unity government (1970-1973). Then, we examine the breakdown of female revolutionary identity during the violent repression known as the military dictatorship (1973-1990) after the coup d’état. Finally, we investigate the reconstitution of the identity of the women on the political left, a process assumed independently (rather than collectively) by women of varied characteristics and political orientations during the re-democratization period and until 2006. By analysing the female characters moving in literature, theatre, and film, we observe that these characterizations have helped to inform the readers/viewers through sharing stories of women, their limitations, their personal and collective visions presenting their doubts and fears on matters pertaining to them as female entities. But the greatest finding in this study is to discover that cultural products contain a number of female characters that can overcome their limitations in fiction, as is the case for women working in public spaces such as Michelle Bachelet, a “historical character” from The General's Daughter. They are firmly committed to the reality of women’s lives in Chile and deliver an optimistic message; women must continue integrating other women in order to end the discrimination that still exists in Chile.