The wilderness, in the form of forest, and the civilized court of knights and ladies often appear as binary oppositions in medieval European romances. The mythical inhabitant of the wilderness, the wild man, in turn, has been considered an oppositional figure to the knight. This essay tries to explicate the relationship between these oppositions by exploring two fourteenth-century Middle English romances where the courtly knights become wild men. In Ywain and Gawain the court and its representative knight are not the norm according to which wild-man figures and even an animal define themselves. Rather, Ywain not only compares badly against the monstrous shepherd of the wilderness, but also regains his knightly identity with the aid of a beast whose various images overlap with those of the knight himself. In Sir Orfeo, the harper-king exiled in the wilderness is empowered and able to restore his queen as well as his kingdom when he recognizes the element of brute force and death in a fairy hunting scene. It is my contention that the experience of wildness in the wilderness by the courtly knights align them with the force of nature that in turn empowers their civility and courtliness.