This chapter examines the representation of the prostitute character in Russian film from the Soviet period up to today, with a focus on perestroika-era and post-Soviet feature films. The chapter examines the importance of the character as an everywoman figure, used by film-makers to explore issues of economic transition, social turmoil and gender. It also highlights the differences and similarities between the depiction of the prostitute in Soviet vs post-Soviet films and the evolution of the aesthetic and thematic depictions of prostitution since 1991. Some films featured in the analysis include Oleg Frelikh’s The Prostitute (1926), Petr Todorovskii’s Intergirl (1989), Aleksei Balabanov’s Brother 2 (2000), Iurii Moroz’s The Spot (2006) and Andrei Konchalovskii’s Gloss (2007). The films analysed in this chapter utilize the prostitute in a way that signals not only her normalization as a fixed figure in contemporary Russian life, but indicate the perpetual use of her character since the early twentieth century to represent destabilizing forces in Russia.