Hollywood cinema offers multifaceted perspectives of the south and the southerner, guided as much by the time of production as by the personnel working on individual movies. This article will focus specifically on two films, fifteen years apart, featuring the same leading actor–James Stewart–in two similar yet distinct portrayals of southerners. The similarities and divergences between the protagonists of Winchester ’73 (1950) and Shenandoah (1965) allow us to explore (via a close reading of each text) specifically how the Confederate rebel was constructed for a national audience in the mid-twentieth century, and how that changed across a contested period that saw wide-ranging events in the battle for Civil Rights. Finally, the article shows how debts and divergences from the nineteenth century logics of white supremacy and secessionism factor into particular Hollywood discourses about geography, whiteness, and masculinity and retain an ongoing relevance in the current, fraught political climate.