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The late Victorian pantomime role of principal boy can be and sometimes was seen as existing outside established gender categories, even as actresses performed in exaggerated fashion some of the markers of both femininity and masculinity. Whether defeating villains, introducing a parade of national types, or leading the audience in song, the cross-dressed principal boy also served as a focal point for fantasies of Englishness. I focus on an 1899 Drury Lane pantomime production of “Jack and the Beanstalk,” specifically the ways that contemporaneous anxieties about the Second Boer War resonate in the panto’s trademark forms of spectacle and burlesque. Drawing on the panto script and accounts of the production, I argue that the principal boy’s ambiguous relation to gender categories positioned her as an apt embodiment of the ambitions, desires, and anxieties of “empire” at the fin de siècle.