Sheila Bock (Interdisciplinary, Gender, and Ethnic Studies) co-guest edited a special Issue of the peer-reviewed and open-access Journal of Folklore and Education titled “Teaching with Monsters: From Whimsy to Shadow.” This issue seeks to create space for the broad spectrum of ways we as humans interact with monsters. While most often associated with fears and anxieties, monsters can also serve as entry points into other dimensions of the human experience, including playfulness and creativity. Together, the contributions to this special issue showcase some of the diverse ways that teaching with monsters can help learners of different ages and in different educational settings develop skills of close reading and critical analysis; navigate ontological uncertainty; and creatively reimagine the world we live in and our place within it.