In this article, we focus on the Tooth Fairy legend that emerged in the United States and Britain in the nineteenth century and on the bedtime rituals associated with it. Drawing on various children’s books, we present this legend and these rituals as among the many legends and rituals found around the world for dealing with the loss of baby teeth in early childhood. Our particular concern is with some of the psychological issues that are associated with the development of teeth in the second stage of infancy. We also draw on the clinical observations of Erik H. Erikson, as we focus especially on the role that teeth play in the loss of the original unity between the infant and its mother. We take note of Erikson’s suggestion that this is, ontogenetically speaking, the experience that is portrayed in the biblical story of the Fall and expulsion from the Garden in Genesis 3. We view the rituals associated with the Tooth Fairy legend as a mythological means of enabling children to address and work through these psychological issues.