Welcome to the American Journal of Play special issue on play in the ancient world, another in the series of theme issues we publish from time to time. Each focuses on an important topic in the fast-developing study of play. Each is guest edited by a distinguished expert on the topic. And each includes work by the leading researchers and thinkers on the topic. For this issue, guest editor Thomas Banchich has assembled a series of articles exploring what we know about play in ancient Greece and Rome and how we come to know it. We begin with two interviews. The first discusses play in ancient Greece with Simon Goldhill, and the second play in ancient Rome with Garrett Fagen, and together they include such topics as theater and comic literature, philosophy and social wit, and what jokes, leisure pursuits, and laughter in the two ancient cultures reveal about them. Our guest editor himself considers how the Greeks perceived playfulness; Dion and Marion Sommer compare ancient and modern toys; and Stephen E. Kidd argues for the seriousness of playful ancient episodic novels as a genre. We have also included a complimentary piece written by medieval scholar Andrew Higl, who examines a tenth-century collection of riddles written in Old English, some of which derive from ancient Greek sources. Taking note of what about play has changed and what has remained the same, these interviews and articles offer insight into the historically contingent nature of play and how it illuminates both ancient sensibilities and our own.