This article describes how a particular kind of queer figure moved from private photography into the mainstream of East German visual culture. It begins with a set of private photographs from the late 1960s from the collection of Heino Hilger, a regular, with his friends, at the East Berlin bar Burgfrieden. The photographs show how dressing in drag and the act of photography were important ways of constituting a gay male subculture. After the decriminalization of sex between men in 1968, the gay scene became bolder and more political in East Germany. The subversion of gender norms was central to the activism of groups such as the Homosexual Interest Group Berlin (HIB) and Gays in the Church. The visibility of the queer figure culminated in the late 1980s, when parts of the film Coming Out were filmed in Burgfrieden and when the popular monthly Das Magazin published a three-part feature on male homosexuality. What all these cultural artifacts and events had in common was not just a critique of the heterosexual norm, but also a queering of the boundaries between masculinity and femininity.