This thesis investigates how we can better appreciate the Roman concept of culpa without incurring in a contemporary falsification of its original rationale. Using a revisited version of Quentin Skinner’s contextualism in light of Gadamer’s hermeneutics, it proposes a deep immersion into the uses of culpa by authors representing different forms of literary expression: Plautus (comedy), Catullus (neoteric poetry), Lucretius (philosophy), Cicero (rhetoric) and Ulpian (jurisprudence). This selection is justified not only by their diverse literary achievements, but also by the satisfactory state of preservation of their writtings. The aim of the thesis is neither to blend these disciplines into a unified narrative, nor to perform an evolutionary inquiry of the legal notion of culpa, an approach exhaustively pursued by great Romanists albeit based on limited data and much speculation. Instead, this thesis looks at specific authorial interventions to understand the concept as close to the original authors use as possible. This approach flows from the understanding that culpa was not used in Latin literature as an abstract notion, but was in fact explored in various contexts involving conflict and judgment.