This work presents some thoughts on Play, Illusion, Reality, and Trauma in relation to the process between patient and analyst. A creative part of our journey in this discussion includes a look at the long career of Charlie Chaplin, in terms of his relationship with his audience as a metaphor for the analyst as audience to his patient and vice versa. Patient and analyst, audience and artist, are mutually and hopefully salubriously intertwined as "involved witnesses" with each other's communication, be they verbal or non-verbal. The level at which these communications are reacted to, the attributions made about them, the connectiveness created, and the therapeutic value derived in the case of analysis, depends on many idiosyncratic factors, both external and internal to the participants involved. I will provide some examples of these factors, both clinical and artistic. In the process, I will define and elaborate the clinical relevancy of play and the concept of a "Playing Alliance" vs "Working Alliance," as well as the irrelevancy of play at certain moments therapeutically. I will also discuss the idea of an aesthetic therapeutic contract and the differentiation of enactments from what I have come to term "actments," (Brok 2014, 2016), as well as the paradox of reality, illusion and the effects of trauma in human experience.