The relationship with the past is complex and almost always conflictive. Events obtain their meaning only a posteriori, relying on a process of signification in which gaps are opened and silences are installed, all at the same time. It is through the archive, a repository of traces and fragments, that the contours and scope of the understanding of the past are traced. As such, the image of the past is constructed through the fabrication of narratives that influence not only perception of historical events but also the sense of identity and memory, both individual and collective. Theoretical contributions of authors such as Walter Benjamin, Ernst van Alphen, Georges Didi-Huberman and Gerhard Richter will be explored in this essay, regarding the reanimation of images from the past as critical acts that question knowledge production. This framework will be specifically addressed to explore the memory of the Portuguese dictatorship (1926–1974) through artistic practice, in this case, through the appropriation of photo albums from that historical period, from different sources such as the personal, the anonymous or from national archives. The work of Portuguese contemporary artists Manuel Botelho (1950), Daniel Barroca (1976), Susana de Sousa Dias (1962) and Filipa César (1975) will be examined, in order to explore the limits of representation of historical memory and experience, the dynamics between the individual and the collective, reality and fiction, the ambivalence of visual documents regarding the construction of meaning, and the use of remembrance as a productive and critical process.