This article conducts a comparative analysis of On the Road (1957) and RuPaul’s Drag Race (2009–present). It is argues that both texts seek to represent a real that is transgressive and empowering. But in order to achieve this representation within a format that will be acceptable to the imagined audience, these texts must perform a problematic process of recording and constructing content. Furthermore, this palatable version of the real excludes aspects of gender and sexuality that are seen to transgress the existing social matrix of acceptable behaviours and identities. This comparative study suggests how recording and presenting the real continues to be problematic, even across time periods and media modes. It also indicates how supposedly transgressive texts may ultimately prioritize marketability over a reality that is truly paradigm-shifting and inclusive.