This article considers current and proposed restrictions placed on the adult industry in Chicago in order to explore the attempts made through legislation to control legal forms of sex work, specifically exotic dancing and burlesque. I focus specifically on the recent debate within the city of Chicago as to whether or not alcohol should be allowed in places where women are topless. While exotic dance is often discussed as a type of exploitation and a cause of urban blight, burlesque is uniformly discussed as positive and empowering, which affects discussion around the introduction of alcohol into each respective club. I conclude by discussing the possibility that the differentiation between exotic dance and burlesque may be a false dichotomy, and that regulations need to be talked about in conjunction with individuals who work in these industries, instead of the assumption that politicians have the laborers’ best interests in mind.