This Element discusses the figure of the cantora – or woman music poet – and the development of her artistic activity in a context of post-colonial paradigms in Chilean and Latin American societies. Through a historical overview of this multifaceted concept, alongside gender construction in colonial Latin America, this Element offers insights on how the figure of the cantora developed in the confluence between discrimination against festive popular culture and the restrictions imposed on women in a context of an inherited patriarchal order. Moreover, it examines the embodiment of the cantora archetype within the contemporary urban folkloric scene in Chile as a performative exercise of identity construction that is framed in a process of cultural resistance. Revealing how contemporary cantoras are continuing the legacy of their predecessors has become especially relevant at the time of writing in 2020–22, amidst a wave of political protests against long-standing social disparities in Chile.