In this address, I will defend a version of an aesthetic hypothesis, which is an idea associated with many philosophers and prominent thinkers. The aesthetic hypothesis is that the way to live a good life, a happy life, is to consider that life as a work of art, and to see that the aesthetic dimension of one’s consciousness, where pleasure is taken from beauty and harmony, is the primary one. I want to argue that those aesthetic values, properly conceived, are at the very heart of being human. I then explain the ‘art of play’ as a doubled phrase in what follows. There is the art of play that is learning how to play or thinking about what it is to play; but there is also the kind of play that is particular to art—not just visual art but aesthetic values in general. I’m going to talk about these ideas along five dimensions. (1) Time – Play at its best takes place within, and allows, that temporal shift. It is the entry into a non-secular time. When we come to talk about finite games we will see how time is both kept and not kept in games. (2) Play – There are many different ways we can conceive of play, and its relation to temporal shifts. Play can be analyzed as a form of socialization, communication, creative imagination, relationship building, and transcendental play. (3) Finite Games – Games and play are not identical categories. Games are organized forms of play. Finite games are games that come to some kind of conclusion. In philosophical terms this outcome would be the telos or final cause of the game—the purpose of the game. (4) Outcomes – What are the outcomes that we derive from finite games beyond winning and losing? At least since Plato and Aristotle, people have believed that the importance of games was that they created a kind of competitive wisdom: agon, the competition-born wisdom of play. (5) Infinite Games – What can we say in conclusion about infinite games and the art of play? We play infinite games in a manner that extends right back to the earliest forms of pretending: We do it, because it is fun. But an infinite game is more than just fun—or perhaps I should say that fun is more philosophically significant than we sometimes think.