Today, whether a worker is legally classified as an employee or an independent contractor determines whether he or she is entitled to employment and labor law protections. With the proliferation of the on-demand economy, the doctrinal definitions and legal analyses of these categories are fiercely contested. While businesses have attempted to confine the definition of employee to limit their financial and legal liabilities and risks, public interest lawyers have worked to broaden the definition, ensuring that more workers are covered and protected by the law. How did U.S. law come to divide workers into these two categories, how have the definitions evolved historically, and how do workers today make sense of them? This Article challenges the duality of worker classification in employment regulation by positioning the employee and the independent contractor in U.S. legal history and in the lives of contemporary workers. Part I situates the debate in work law scholarship. Part II uses historical and legal archives to challenge the prevailing assumptions about the employee and independent contractor classifications in employment and labor law. I argue that the existence of the dualism of worker categories is more recent than previously understood and that contemporary doctrinal tests reflect not bright line legal rules, but evolving political and cultural philosophies about work. Part III investigates the impact of these legal classifications on the ground. Through ethnographic research and analysis, I find that these categories of work have taken on social meaning for workers, often disrupting worker collectivities. The Article concludes that both the doctrinal analyses of the employee category and the lawyering methodologies used to advance the interests of workers must be more attendant to workers' realities.