The work of avant-garde auteurs from the mid-twentieth century onward is a testament not only to Pirandello’s ongoing influence but to the ways artists continue to break open fresh paths, building on Pirandello’s aesthetic. Through the destabilization of day-to-day existence, especially in his theatre trilogy – Six Characters in Search of an Author (1921), Each in His Own Way (1924), and Tonight We Improvise (1930) – Pirandello shatters every kind of theatrical binary. Out of these eruptions, a sense of the postmodern emerges, evoked via the experience of a messy, chaotic collaborative process that culminates in an “anti-play” filled with seemingly random and often sinister playfulness. This essay closely examines the processes and performances of the Living Theatre’s (New York, 1959) and Robert Brustein’s American Repertory Theatre (Cambridge, Massachusetts, 1987) productions of Tonight We Improvise. John Jesurun and Takeshi Kawamura’s Distant Observer: Tokyo/New York Correspondence at La MaMa (New York, 2018) is the next focal point – only one of many current transmittals of Pirandello’s genius, moving forward.