Drag's influence on Head over Heels
Head over Heels plays with the theme of queering the gender binary as it has characters who are nonbinary and characters experimenting with their gender identity. In the original production the drag queen Peppermint played the role of Pythio and made history as the first woman who identifies as trans to originate a role on Broadway. This character was highly influenced by drag culture. What some might find surprising is that not all of the genderplay in Head over Heels is a product of Jeff Whitty adapting the story. There was cross-dressing in the source text. Musidorus pretends to be a woman creating a complicated love triangle between Basilius, Gynecia, and Philoclea. While Musidorus' conclusion at the end of the musical is part of the adaptation this homage to cross-dressing in Elizabethan England actually has more to do with Drag culture than you might think. The following videos give some important context for how Drag culture became what it is today.
History of Drag
Cross Dressing in Elizabethan England
Cross dressing was a common occurrence in Elizabethan fiction so much so that nearly a fifth of all of Shakespeare's plays involve a plot point that require a character to pass as a member of the opposite sex. Cross dressing was seen on stage as well as women were not allowed to be actors. Teenage boys were responsible for playing all the female roles on stage. Cross dressing off of stage was much less permissible however. There are records from the 1500s that show how women were punished for wearing men's clothing. While their reasons were not all the same and spread out across many years it demonstrates that at least some people were trying to present as their preferred gender even in the Elizabethan era. Someone who gained much prominence for wearing men's clothing was Mary Firth or Moll Cutpurse. She dressed as a man for much of her life and gained quite the reputation for her criminal acts. She was so famous that there was even a play written about her reputation and power in the London underworld. While not much is written that would allow historians to write definitively about transgender individuals during this time 17 years after Queen Elizabeth died King James was worried about the effects of cross-dressing that he ordered the Church of England put out pamphlets warning about the perils of cross dressing. This pamphlet demonstrates that cross dressing may have been more common than what written documentation has allowed historians proof of. For more information on this topic feel free to read this article!
Moll Cutpurse