Nostalgia for Prohibition suffuses popular culture of late. The Leonardo DiCaprio film, The Great Gatsby, the very popular cable series, “Boardwalk Empire,” and consumer desire for artisanal moonshine and “bootlegger balls,” all seem to manufacture a newly romanticized 1920s. How do we debunk stories that glamourize speakeasies and gangsters, violence and crime? What are more complicated, nuanced, and realistic narratives of this period? Using Chicago and Illinois as a case study, we will explore how Prohibition spurred an ominous expansion of racialized government policing and surveillance, and swept in a powerful cultural shift toward modernity that also realigned gender roles and expectations.