This article reexamines the well-known debate over the origins of de jure segregation in the American South, which began in 1955 with the publication of C. Vann Woodward’s The Strange Career of Jim Crow. Arguing that the debate over Woodward’s thesis implicates familiar but outmoded ways of looking at sociolegal change and Southern society, the article proposes a reorientation of this debate using theoretical perspectives taken from recent work by legal historians, critical race theorists, and historians of race, class, and gender. This article examines the advent of railroad segregation in Tennessee (the state that enacted the nations first railroad segregation statute) in order to sketch out these themes, arguing that de jure segregation was brought about by a dialectic between legal, social, and identity-based phenomena. This dialectic did not die out with the coming of de jure segregation; rather it continued into the modern era.