This chapter reconstructs Antonio Albanese’s career from its inception in the early 1990s, with the development of the contradiction that would mark his entire work, that between the tragic nature of his characters—inspired by his theatrical studies at the Paolo Grassi School of Dramatic Art in Milan—and the purely comic one—which emerged in his TV sketches. Rereading his monologues today, we see how Albanese’s mask took two main paths. The first regarded a certain schizophrenic gestural mimicry and the use of neologism, which anarchically discarded reality to more crudely reveal the restlessness from which any comic posture is born. Onto this first path a second path was grafted, in which, on the contrary, Albanese pushed the pedal of a more superficial pride that invoked the one thing of which he was certain: being male. We can observe that the three-dimensionality of the first path, the complex one of unmasking and making explicit a comic movement bursting with contradictions of a more dramatic type, appeared more in Albanese’s theatrical career, where his bodily presence acquired inescapable depth, than in his movie or television career, where his two-dimensional image of a sarcastic machismo allowed him to remain on the surface.