Historical fiction has long been a staple in the social studies, history, and English curricula of primary and secondary education. Such commercial and critical successes might be linked to the genre's unique ability to blend educational, didactic, historical, and aesthetic concerns in children's literature, aspects that are heightened considerably when authors elect to appropriate Shakespeare in their historical fiction. While some critics suggest that the genre of Shakespeare-for-children advocates discourses of normative gender, identity, and behavior, this study maintains that the ongoing cultural capital of the Bard in the classroom and on the bookshelf permits authors the opportunity to consider unconventional expressions of gender. More specifically, this article argues that authors of late-twentieth century historical fiction about Shakespeare turn to the early modern tradition of boy players performing as women in order to embrace alternative gendered identities and models of maturation, particularly as they regard boys and boyhood.