In this work I will address the filmic Trilogy of Life as one of the most emblematic and effective expressions of Pasolini’s intellectual intervention in the Italian cultural panorama of the late 60s and early 70s. Through a stylistic and structural analysis, I will focus firstly on Pasolini’s personal understanding of the relationship between a creative subjectivity and the world of the objects that need to be engulfed and shaped in order to be properly represented by the subjective artistic impulse. In the first part of this study, I will identify such a dynamic process of representation with Pasolini’s typical poetics of contamination. In the second part I will utilize the considerations of the first part as a point of access to both Pasolini’s theory of cinema and the practical realization of it in the Trilogy of Life. In the analysis of this cinematic trilogy I will use as a constant point of reference two articles written by Pasolini as defensive commentary and political justification of the Trilogy of Life: Libertà e Sesso Secondo Pasolini and Abiura dalla «Trilogia della vita». Moreover, through a close reading of the three movies of the trilogy – Il Decameron, I Racconti di Canterbury and Il Fiore delle Mille e Una Notte – I will specifically address the dreamlike tone that permeates Pasolini’s three-fold cinematic work and its especially saturated presence in the last movie. In conclusion, I will show how this saturation overturns and undercuts the tone suggested by the title – Trilogy of Life – to produce a trilogy that is more about death than life.