This article analyses cross-dressed performances by women in films produced in the Russian Empire between 1910 and 1917. It examines around 25 films, both those that are extant and those considered lost, and identifies two major groups: cross-gender cast films and films featuring women characters who temporarily disguise their gender identity. In most of the films in the first group, women are cast in the roles of boys and young men, which links them directly to the theatrical travesty tradition. The article devotes special attention to Portret Doriana Greia / The Picture of Dorian Gray (Vsevolod Meyerhold, 1915, Russian Empire), in which the actress Varvara Ianova played the eponymous role. It also traces some of the public discussions on the topic of travesty in Imperial Russian theatrical circles, focusing on a 1905 brochure Pochemu ia igraiu rol’ Orleanskoi Devy / Why I Play the Part of the Maid of Orleans by Boris Glagolin, an innovative theatrical actor and director who indeed portrayed Joan of Arc on stage. Among the films that depicted cross-dressing as intrinsic to the plot, the article briefly reviews several comedies, as well as dramas in which cross-dressing was less widely represented and usually included as part of a heroic narrative. The film Nelli Raintseva (Evgenii Bauer, 1916, Russian Empire) represents a remarkable exception to this trend and is therefore analysed more closely.