While frequently associated with crushing seriousness and austere leadership, the Christian church in the medieval period was a surprisingly fruitful arena for the development and enjoyment of humor. While the early church took a more negative stance toward the topic, key thinkers who shaped the medieval European worldview saw the world, life, and existence itself as a gift, and something in which to delight, and from that delight flows laughter and humor. This chapter discusses the presence of laughter and humor in the Bible, the predominantly negative view on the topic among the early church fathers, and the shift to seeing humor and laugher as a part of delighting in the world as seen in St Augustine and later thinkers.