In this study, we present an analysis of the Valparaiso's urban imaginary present in both novels Dos hombres y una mujer. Memorias de un proletario (1933) and La estrella roja (1936). For this purpose, we study how Jacobo Danke's narrative, published in the 1930s, puts in crisis the traditional representation of the city. Using theoretical resources from the literary theory, anthropology, philosophy and history, we demonstrate that emerges an "anarchic city" from Danke's narrative. The latter is characterized by disorder, dissent and hostility that mark the opening of Valparaiso's extensive cycle of decadence in the twentieth century.