The turn of the 20th century was a time of major political and economic fluctuation and demographic shifts in American cities. As a result, physical health and physical supremacy became serious concerns. Between 1880 and 1930, the Progressive Era, politicians, doctors, and educators advocated for physical activity with the intent to improve individual living conditions, health, and well-being. Exploring the history of the playground movement provides insights into the impetus for legalizing physical education in American public schools. In this paper, we examine the complexity and multiplicity of competing educational and political discourses emerging from the playground movement at the turn of the century--civilized play and democratic play. Democratic play provides an example for physical education researchers and physical educators about creating and sustaining progressive physical education curricula and adopting pedagogies that "unsettle the body" to subvert the racial and gender order in physical education classes today.