The popularity and availability of Ernst Lubitsch’s cross-dressing comedy Ich möchte kein Mann sein (1918) sometimes creates the impression that it is a unique example of female-to-male cross-dressing in silent cinema. Likewise, attention to the gender and sexual play of Weimar-era (1918-1933) German cinema often eclipses cinema of the Wilhelmine era (1895-1918). This article asks: how does Ich möchte kein Mann sein fit into the wider ecology of German films featuring cross-dressed women, during both the Wilhelmine and Weimar eras? How are the cross-dressed women of German silent cinema similar to and different from silent films in other countries? After examining more than 47 German silent films featuring cross-dressed women, I argue that German films adapted transnational cross-dressing performance traditions to fit local contexts, offering audiences deliberately contradictory experiences of female masculinity and same-sex desire. Though scholars have focused on Weimar cinema as offering new possibilities for gender and sexuality, Wilhelmine cinema also offered varied visions of female masculinity – especially in Danish actress Asta Nielsen’s creative takes on cross-dressing traditions. Weimar films continued these traditions while making more explicit reference to real life lesbian and gay subcultures. Attending to the complexities of female-to-male cross-dressing allows us to see how popular culture envisions alternative gender and sexual scenarios while maintaining its popularity and, for the most part, dodging the censors’ scissors.