This dissertation is a comparative study of three contemporary women filmmakers: Puerto Rican Frances Negrón-Muntaner, Chicana director Lourdes Portillo, and Brazilian director Helena Solberg. Informed by transnational theory, politics of location, feminism on the border, and approaches to documentary filmmaking, the study examines three filmic texts: Brincando el charco: Portrait of a Puerto Rican (1994), The Devil Never Sleeps/El diablo nunca duerme (1994), and Carmen Miranda: Bananas Is My Business (1994). Each film is narrated by a female voice who juxtaposes her personal and transnational identity with history to tell her migration story before and after returning to her country of origin. An objective of the study is to demonstrate how the film directors vis-á-vis their female protagonists, configure a United States Latina transnational imaginary to position their female protagonists and themselves as female directors and as active social agents. Further, the dissertation explores how the filmmakers construct, utilizing the cinematographic apparatus, specific forms of resistance to confront certain oppressive forms. The theoretical framework proposes that transnational documentary filmmaking offers specific contestatory representations and makes possible the opening of parallel spaces in order to allow for a transformation from multiple perspectives. Through the utilization of specific techniques such as archival footage, the three directors focus on historical biographies. Further, they make use of experimental filmmaking and, in particular, the transnational documentary to deconstruct hegemonic discourses. Lastly, transnational cinema is valued as a field for cultural renegotiating and as a result, the documentary filmmakers in this study are able to reconfigure a transnational imaginary and propose an alternative discourse about history, sexuality, family structures, and gender relations. In sum, my dissertation contributes to Chicana/o and U.S. Latina/o, American Literature, and other Ethnic Literatures by focusing on migration, acculturation, and multicultural dialogue.