What happens if we think of children's play as a form of great art that we turn to and return to for inspiration, for education? If we can see play as art, then what and how can we learn from children's play or from playing with them? What can philosophy, or philosophers, learn from children's play? In this essay Viktor Johansson gives examples of what and when children can teach philosophers through play or, more specifically, how children's play can teach philosophers about the relation between fiction and reality. It begins by exploring the educational relation between fiction and reality in recent revivals of literary humanism. Johansson gives examples from a preschool project of how children use fiction picture books and create new fiction in their play, and how they do so in ways that relate to previous philosophical considerations of literary fiction. To explore this, the essay enters into conversation with the work of Iris Murdoch on the playfulness of art. Through, and in contrast to, Murdoch's work, Johansson establishes that play can be great art through its nonpurposefulness and its use of skill and imagination. Moreover, turning to children's play becomes a method for attending to what Ludwig Wittgenstein calls philosophy's natural history, that is, a historicization of philosophical thinking that enables philosophers to learn from children. Johansson concludes by showing that encounters between fiction and play, and with children playing, can be an educational embroilment, not only between teacher and child, but between teacher, child, the visual, the material, and the philosophical in which all learn from one another.