This photo essay describes the life and work of self-taught itinerant portrait photographer Hugh Mangum (1877–1922) and includes a selection of his black-and-white glass plate negatives—many damaged by neglect and the passage of time—scanned and reproduced in full color with the aid of twenty-first century digital technology. Working primarily in North Carolina and Virginia, during the rise of the segregationist laws of the Jim Crow Era, Hugh Mangum welcomed a clientele that was both racially and economically diverse. Using a Penny Picture camera that allowed him to record multiple separate exposures on a single glass plate negative, he left behind an unintended record of the succession of sitters who passed through his traveling studio. These multiple image plates depict a wide variety of people, confounding the common historical narrative and hinting at unexpected relationships and complex lines of connection that refute the racial categories defined by law to separate black and white people. Hugh Mangum's strikingly detailed and democratically seen portraits offer an unusual sightline into a turbulent time in the history of the southern United States.