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The present study aims to investigate the psychological mechanisms behind the change in the facial expression of some of the beheaded characters in Caravaggio’s works, starting from The Head of Medusa, from the artist’s youth, and up to David with the Head of Goliath, a mature workpiece, searching the continuity between them through a series of self‑portraits/ self‑insertions of the artist in his work. The psychodynamic analysis I propose is limited by the constitution of its practice to the study of the process of image production and the artistic imaginary, rather than to the investigation of the man or the artist, who is out of reach, by means of figurative and symbolic language. This approach aims to highlight the drives of the unconscious, the structures of censorship and the operating technique of the defensive mechanisms that ultimately could contribute to the production of such masterful images that are both seductive and confusing. The study incorporates and continues the contribution of authors such as Leo Bersani and Ulysse Dutoit, who applied Laplanche’s theory of generalized seduction in the analysis of Caravaggio’s works, but also the mirror stage of Lacan and the masterful study of Donald Winnicott regarding the reflection of the baby in the mimics of his mother, an unconscious unclear image that will stand forever for the perception of the self. The change of the affective resonance, expressiveness and emotional relating to violence is natural in the course of human evolution. While not even the artist Caravaggio can elude it, his work can illus‑ trate by deflection these transformations of the dynamics of the mind, it can raise new questions and open new perspectives of understanding the artistic drive. [ABSTRACT FROM AUTHOR]