Celebrating Sorrow explores the medieval Japanese fascination with grief in tributes to The Tale of Sagoromo, the classic story of a young man whose unrequited love for his foster sister leads him into a succession of romantic tragedies as he rises to the imperial throne. Charo B. D'Etcheverry translates a selection of Sagoromo-themed works, highlighting the diversity of medieval Japanese creative practice and the persistent and varied influence of a beloved court tale. Medieval Japanese readers, fascinated by Sagoromo's sorrows and success, were inspired to retell his tale in stories, songs, poetry, and drama. By recontextualizing the tale's poems and writing new libretti, stories, and commentaries about the tale, these medieval aristocrats, warriors, and commoners expressed their competing concerns and ambitions during a chaotic period in Japanese history, as well as their shifting understandings of the tale itself. By translating these creative responses from an era of uncertainty and turmoil, Celebrating Sorrow shows the richness and enduring relevance of Japanese classical and medieval literature.