In ‘Ride With The Devil’ the Boundaries Between North and South and Slave and Free Blur

American history, culture, and identity have traditionally been interpreted through the lens of “difference”, especially the difference that exists between opposites. In its pursuit of an orderly society, the antebellum and Reconstruction South relied heavily upon categorization based upon such “difference”. Consequently, when it comes to the American Civil War, filmmakers have offered up a plethora of binary oppositions from which audiences can find and make meaning: North over South, black over white, man over woman, free over slave, hero over villain, winner over loser.

Director Ang Lee, avoids all such convention in Ride With The Devil. Artfully transcending the dualisms associated with the American South, Ride With The Devil is an exception to the Civil War genre. It is also an exceptional film.

Based on Daniel Woodrell’s novel, Woe To Live On, and adapted for the screen by James Schamus, Ride With The Devil tells a story of the Civil War from a rather unusual perspective. At the center is teenager Jake “Dutchy” Roedel (Tobey Maguire). The son of German immigrants, Roedel belongs to a band of ruthless Missourian guerrilla fighters known as bushwhackers. Like the historical figures upon which both film and novel are based, these Missouri Irregulars sympathize with the South, but swear no allegiance to either side.

Here lies the first of several simple dichotomies that Lee’s film debunks. Contrary to how the Civil War is typically understood, not all those who fought did so in the name of the Union or Confederate army. Nor, as in the case of the bushwhackers, did bloodshed always occur in service to an overarching ideal. For Roedel and the rest of his gang, their relation to the war, and the terror they inflict, seems to have more to do with friendships and happenstance than devotion to some noble cause.

Ride With The Devil offers understated performances from a cast of talented actors, including the singer Jewel who stars in her first and only film as the war widow, Sue Lee Shelley. Other members of Jake’s crew include his childhood friend, Jack Bull Chiles (Skeet Ulrich), the sociopathic Pitt Mackeson (Jonathan Rhys Meyers), George Clyde (Simon Baker), and Daniel Holt (Jeffrey Wright), a former slave whose freedom was purchased by Clyde.

The long history of representing black people includes some of the most memorable Civil War films, and demonstrates that reliance upon “difference” breeds an over-simplification of meaning that can reduce a group of people to a few essential traits. Gone With The Wind (1939) has its mammy (Hattie McDaniel), Alex Haley’s Queen (1993) has its tragic mulatto (Halle Berry), and Glory (1989) has its restive buck (Denzel Washington). As film historian Donald Bogle points out, America’s crowning achievement in film, The Birth of a Nation (1915) gives us all of the above stereotypes with a couple more thrown in for added emphasis.

Daniel Holt is Ride With The Devil’s only African-American character. As embodied by the brilliance of Jeffrey Wright, Holt communicates a superbly nuanced and dignified representation of blackness not found in other Civil War films. In fact, despite his limited dialogue, Holt is arguably one of the film’s most complex characters, and his presence onscreen further complicates simplistic notions of the Civil War.

In Ride With The Devil, not only are the boundaries between North and South made hazy, but through the character of Holt, the lines between slave-and-free, and black-and-white are also blurred. While other films offer accounts of slaves who escaped to join the Union Army, Ride with The Devil gives us a freed slave who fights with the Missouri Irregulars. Both accounts may be true to history, but presumably, because it doesn’t fit within reductive thinking, a black man fighting for the South is a story that is largely ignored. Make no mistake, though, Holt’s allegiance with Southern sympathizers, does not render him a sellout.

Holt is simply a man deprived of family, who follows his childhood friend to war. Toward the end of the film, after Clyde dies in battle, Holt reveals to Roedel the nature of his relationship to George Clyde:

Holt: That day George Clyde died, it changed me. I felt something that day I ain’t never felt.

Roedel: You felt that loss, that hollow feeling.

Holt: No, what I felt was free.

Roedel: I thought that’s what George gave you when he bought you out.

Holt: That wasn’t really his to give now was it? George Clyde, I believe I loved him, but being that man’s friend wasn’t no different than being his nigger. And Roedel, I ain’t never again gonna’ be nobody’s nigger.

Even though Holt’s freedom has been bought, for much of the film, he is still not “free”. Holt’s motivations are largely explained by the historical moment and oppression that comes under the guise of freedom.

Ride With The Devil is a film that resists narrative convention. The audience is not enlisted to help solve any problem, there is no end to the war, no intended destination, and it’s not entirely clear for whom we should be rooting. There is always a price to be paid for bucking convention. Lee paid that price at the box office. The theatrical release of Ride With The Devil in 1999 was a failure.

Without some of the devices we rely upon to make meaning, viewers probably had difficulty making sense of Ride With The Devil. That was certainly true for me after my first viewing. Once I accepted, however, that certain conventions had been abandoned, watching the film for a second time was a different experience. I was able to simply settle in with the characters, appreciate their clever dialogue, their place in history, and relish the pictorial quality of the film’s landscapes and changing seasons. Ride With The Devil is one of those films that becomes more enjoyable with each subsequent viewing.

The new director’s cut from the Criterion Collection has a wealth of extras that will appeal to history and film buffs alike. First, there are two audio commentaries. One features Lee and Schamus. The second commentary features cinematographer, Frederick Elmes, sound designer, Drew Kunin, and production designer, Mark Friedberg. The DVD also includes an interview with actor Jeffrey Wright who discusses his portrayal of Daniel Holt. Finally, there is a booklet featuring essays by critic and filmmaker Godfrey Chesire, and historian Edward Leslie.