This dissertation examines iconic murders committed by four Chilean women: Corina Rojas (1916), Rosa Faúndez (1923), Carolina Geel (1955), and Teresa Alfaro (1963). Their crimes not only led to the passing of substantial court judgements, but gave rise to multiple cultural reverberations: novels, poems, short stories, artworks, plays, songs, and films, produced and reproduced throughout an entire century. Based on the discovery and analysis of the four judicial rulings and a close examination of their various cultural echoes, this thesis interrogates the normative power of the representation of violent women. In other words, this dissertation proposes that both legal and cultural representations of female criminals serve as mechanisms to monitor the compliance of gender norms, to punish their transgression, and to prevent further subversions. The study of these four cases and their cultural reverberations allows for a critical examination of enduring feminine archetypes –the witch, the madwoman, the jealous woman, the hysteric, and the femme fatale– which deprive women of agency. Furthermore, this dissertation revisits the history and myth of La Quintrala, key in the construction of Chilean identity, as a figure that influences the fates of this unfinished series of female outlaws. Hybrid and interdisciplinary, this research questions the representation of deviant women from a feminist perspective, and examines female violence as a privileged site to analyse issues of race, class, gender and nationhood in Chile.