The rise of children's literature, for example, as a distinct classification of books in the seventeenth and eighteenth centuries, woven into the fabric of an increasingly affluent middle class, contains within it the histories of children's play and children's mental health. This chapter explores some of the stereotypes as well as the slightly more nuanced images of mental illness found in children's literature and film, specifically in the added context of children's play. A broad historical consensus has come to exist regarding the importance of play and games to the physical and psychological well-being of a child. As one of the nineteenth century's preeminent books, Alice's Adventures in Wonderland is an appropriate place to begin a more detailed discussion about madness, mental illness, and play. The use of toys in Toy Story to explore themes of mental illness, children's play, and family life echoes a much broader conversation in the 1990s about toys, mental health, and childhood.