Pyotr Tchaikovsky’s early opera Oprichnik is overdue for rediscovery as one of the composer’s most overt forays into the queer themes that critics and scholars have long appreciated in his mature works. Oprichnik features the composer’s most extensive and provocative employment of travesti in its depiction of a historical figure mostly remembered for his rumoured sexual relationship with tsar Ivan IV. This paper takes a detailed look into this and other queer features of the opera within their cultural, historical and biographical contexts. These contexts, including the development of trouser roles in Russian opera, transformations in public discourse on sexuality and gender, and Tchaikovsky’s relationship with his pupil Vladimir Shilovsky, help bring into focus the special appeal the sixteenth-century Muscovy of Ivan the Terrible and his oprichniki had as a topos for a Russian artist experimenting in the artistic depiction of sexual and gender variance.