This episode examines the issue of play. What is at stake in play? How do "rules of the game" relate to the freedom of play? The second segment turns to the notion that aesthetic pleasure arises for Immanuel Kant from the "free play" of the Imagination and Understanding that exhibits "lawfulness without a law." I suggest that in both play and this notion of aesthetic judgment the "law" or the "rules" are emergent--they emerge out of the act of playing, they are in play. The last segment looks at bebop as a form of play and confronts the Kantian paradox that some limited civil unfreedom leads to greater artistic and intellectual freedom.