For the Stratford Festival of Canada, the years 1994 to 2007 were largely defined by the figure of artistic director Richard Monette, whose ambitious seasons performed spectacularly at the box office but whose populist showmanship stirred debates about the aesthetic appropriate for a classical theater company. This article assesses Monette’s artistic directorship and considers the future of what the new leadership has rebranded the Stratford Shakespeare Festival. It modifies the view that Monette was a populist who privileged the box office over artistic integrity, stressing instead the aesthetic diversity of Monette’s Festival. It examines, too, how Monette responded to criticism by increasing the diversity of his casting and programming. The article further explores the intentions and the spectacular disintegration of the three-person directorate appointed to replace Monette and it considers the early decisions of the sole remaining artistic director, Des McAnuff. While the demise of the group leadership model reduces the likelihood of truly radical change, the article suggests that McAnuff will nonetheless make a difference, especially in pursuing more dynamic approaches to directing Shakespeare and structural changes to the revolutionary Festival Stage. The article argues that even as Stratford moves forward, Monette’s tenure remains a major context for understanding the fraught transition that followed him and the ongoing changes that seek to redefine the Festival as a state-of-the-art theater for the twenty-first century.