Considering the life and work of Goliarda Sapienza in the 1980s, a critical discourse emerges that contextualizes first her eccentric and nonconformist views on women’s roles during the historical transition to difference feminism. The specific matrices of “freedom” that critics have already identified, and the roles of some institutional and intellectual figures she approached during that period, including Adele Cambria, are certainly noteworthy. A second field of analysis will consider the autobiographical prison volumes published in 1983 and 1987, L’università di Rebibbia and Le certezze del dubbio, with greater attention to defining the role of Roberta as a former political brigatista, comparing her to other characters proposed by literature and cinema in contemporary and more recent years: consider the novel Nucleo Zero by Luce d’Eramo (1981) and the films Marianne and Juliane by Margarethe von Trotta (1981) and Segreti, segreti by Giuseppe Bertolucci (1984). In particular, an attempt will be made to also define the content-related reasons that may have excluded the 1987 novel from editorial destinations different from the one the author arrived at, namely Pellicanolibri.