Shakespeare was keenly affected by the lives of the boys who played the parts of women in his plays. Evidence for his understanding and compassion is found in the speeches of those characters who cross-dress female to male. By a double negation of his gender, the boy actor is given an opportunity to speak for himself as well for the female character he is portraying. The examples are Julia as Sebastian in The Two Gentlemen of Verona, Portia as Balthazar and Nerissa as both the young lawyer’s clerk and Jessica in The Merchant of Venice, Viola as Cesario in Twelfth Night, Imogen as Fidele in Cymbeline, and especially Rosalind as Ganymede in As You Like It. I argue that what they were given to say by Shakespeare reveals the experience of being a boy, not only in early modern England or ancient Greece (where all parts were also played by males), but also in our time. I suggest the treatment of boys in the theatre is mirrored by the treatment of boys today. In those instances where doubled impersonation was written into Shakespeare’s plays, we have a unique opportunity to hear boys tell us about themselves. As with so much else that is timeless insight, the bard understood and articulated the experience of being a boy. Taken together, the utterances of his “boys” tell us how it is to be a boy.