Abstract: This article reexamines the well-known debate over the origins and timing of the advent of de jure segregation in the American South that began in 1955 with the publication of C. Vann Woodward's The Strange Career of Jim Crow. Arguing that the terms of the debate over Woodward's thesis implicate familiar but outmoded ways of looking at socio-legal 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 America's 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 the the coming of de jure segregation, but rather continued into the modern era.