Even though Shakespeare’s plays were initially performed by all-male casts, they were designed to appeal to diverse audiences. Many modern adaptations reimagine those plays as expressions of gender nonconformity. Over the past decades, prominent films and theater works have fostered new public conversations about the politics of appropriating gender identities in Shakespeare’s plays around the world. This chapter makes an intervention in both transgender and Shakespeare studies by reading traditionally binary characters as transgender to shed new light on performances of gender identities in a global context. Viola as Cesario, for instance, is a trans masculine character, as she does not cross-dress for entertainment or mischief. She never recovers her “maiden’s weeds” at the end of Twelfth Night. We could deploy transgender theories to examine other cases as well, such as the practice of cross-gender casting (Julie Taymor’s 2010 film The Tempest), gender-bending performances (contemporary productions of Jacob Gordin’s 1898 play The Jewish Queen Lear), and postgender adaptations, in which gender is not treated as a meaningful denominator of characterization (Michelle Terry’s 2018 Globe productions). Performance theories inflected by transgender studies destabilize the line between normalcy and the deviant in and beyond scripted performance. ::::: https://rowman.com/ISBN/9781683933601/Performing-Shakespearean-Appropriations-Essays-in-Honor-of-Christy-Desmet