William Lily was Tudor England's most famous grammarian. His Latin grammar, developed while he was master at Saint Paul's School, became England's national grammar. Shakespeare learned his small Latin from Lily's grammar, and he makes quibbling references to it in Love's Labor's Lost (performed circa 1595) and Twelfth Night (performed 1601); generations of English writers after him learned how to make sentences from Lily's syntax. Polydore Vergil exaggerated when he styled Lily the first to bring Latin eloquence from Italy to England, but he was not alone in his opinion. In Tudor England, Lily's Italian learning set him apart; abroad, he was known for his poetic wit, his knowledge of Greek, and his abilities as a translator.

Lily was born at Odiham in Hampshire, probably in 1468. Virtually nothing is known of his youth before 1486, when he was admitted demy (or foundation scholar) of Magdalen College, Oxford. The Magdalen of Lily's...