James Joyce’s artist-hero, Stephen Dedalus, seems to live in a universe that teems with grotesque female monsters, from the Classical Gorgon to the sexually aggressive New Woman. It is a world that resembles the mythic early Ireland depicted in medieval manuscripts, replete with loathly ladies. The archetypal loathly lady developed into a distinctive figure in medieval Irish and English literature: the shape-shifting Sovranty Hag. These symbolic female characters are imbued with the potential to transform both themselves and their chosen consorts into something lovely and powerful through the fulfillment of a quest. The artist-hero Stephen stumbles in and out of several recognizable loathly-lady quests in A Portrait of the Artist as a Young Man and Ulysses . This article examines the amalgamation of Irish and English medieval tales of Stephen’s unresolved quest as well as the significance of Joyce’s revival of the powerful medieval loathly lady.