This essay is a study of the art of play as it is defined and used in my musical performance practice. In three sections, I will discuss the nature of play, including examples of what I am defining as the “performance of play.” Next, I will look at a case study of how these ideas are incorporated in the popular 1980’s television show Pee-wee’s Playhouse. Lastly, I will discuss how this performance practice is applied to my own work through recent collaborative project, Pocket Music.