This article investigates the teaching of rhetoric as a discrete discipline within the curriculum of Tudor-era English grammar schools (such as the King's New Grammar School in Stratford-Upon-Avon, where William Shakespeare is believed to have been educated). It examines more recent attempts to advocate for the value of rhetoric as a unifying principle guiding and informing how and why we educate; it also identifies links between these recent attempts and a Tudor-era understanding of "imitatio" (one aspect of rhetoric) arguing that these links can inform pedagogical practice and the interpretation of curriculum for today's English teachers, particularly for the teaching of Shakespeare. Finally, the article argues that a comparison between a Tudor-era understanding of rhetoric and a 21st-century understanding carries significant implications for how we understand and teach for creativity.