“From Prison Yard to Field of Play: Documentary Histories of Race and Movement in Film, Television and New Media” is a hybrid theory/practice dissertation examining representations of race and history in two distinct but overlapping social spheres in which racial identity is perpetually and prominently being constructed and contested: prisons and professional athletics. It consists of the following components: a pair of written chapters, exploring documentary and commercial media depictions of the boxer Muhammad Ali and the role of the GIF format in the contemporary sports media landscape; a cycle of GIFs depicting Ali; and two short experimental documentaries dealing with two events in American carceral history. Using this diverse array of approaches and objects, I argue that the form and content of narratively determined histories of race and social struggle are often inadequate for addressing questions of racial and political identity and representation in a way that is contingent, non-teleological and non-essentializing. Instead, I advocate for non-narrative scholarly and creative approaches to, and media representations of, histories of race, which emerge from a study of archival moving images, and the historical gestures, movements, and performances they depict. My critique is situated in an analysis of popular historical narratives, as expressed through the form of the documentary film, as well as a broader assessment of the circulation of essentializing racial narratives in the contemporary online media sphere. Overall, this dissertation contributes to and expands the field of historical documentary media production while critically considering the form, format and content of popular representations of race, gender and class, as articulated through sports media and carceral histories.