The purpose of this work is to explore how Luigi Pirandello’s Enrico IV (1922) and Miguel de Unamuno’s El hermano Juan o el mundo es teatro (1929) utilize metatheatrical strategies to create plays that constantly question the juxtaposition, and yet the fluidity, of reality and fiction. Through a similar existential search, which is guided by a Sartrean psychoanalytic approach, the protagonists endure a transformation that reveals contrasting results: Enrico remains entrapped in his theatrical portrayal of Henry IV. Conversely, Don Juan frees himself from societal restraints that had portrayed him as a trickster through centuries of literary tradition. In these plays, authority becomes an ever-shifting device that persistently moves from the author, to the characters, and finally to the audience, affecting their own freedom, intended in the Sartrean sense, and being.