Missouri was one of the slave states that was kept in the Union during the Civil War and since it was on the far side of the Mississippi River it was not really part of the Western Theater of the war. As the critical part of the Anaconda Plan the Union armies were seeking control of the Mississippi, which explained why Grant was fighting his way from Tennessee to Vicksburg while Farragut took New Orleans. In fact, there really was not an organized Confederate army in Missouri, which explains why the young Southern men in "Ride with the Devil" join the Irregulars, who waged guerrilla warfare against Union loyalists. In this part of the war we do not talk about great battles, but rather the infamous raid that torched Lawrence, Kansas on August 21, 1863 as Quantrill's raiders murdered the pro-Union jayhawks.
The story here focus on six young men who join the bushwackers: Jake Roedel (Tobey Maguire), a first generation American who wants to be considered as much a Southerner as any one else even though his father can from Germany (which means he is called "Dutchy"); Jack Bull Chiles (Skeet Ulrich), who hates the Yankees and has seen his family killed; George Clyde (Simon Baker-Denny), a gentleman fighting to preserve a way of life that is going to be gone with the wind; Daniel Holt (Jeffrey Wright), an ex-slave who fights besides Clyde because the man freed him; Pitt Mackeson (Jonathan Rhys Meyers), who is a sadist who glories in killing; and Black John (James Caviezel), almost as brutal but more driven by anger and revenge.
The idea in "Ride with the Devil" is that when America went to war with itself in 1861 the young boys growing up in Missouri and Kansas were suddenly forced into a less than honorable manhood overnight. Consequently, one of the first casualties of the war was their innocence. In 1987 Missouri-born author Daniel Woodrell wrote his Civil War-era novel "Woe to Live On." For Ang Lee the appeal was the drama of young people coming of age in the worst possible time in American history and the theme of self-emancipation. The principal actors were put through three weeks of "boot camp" to capture the way the war dehumanized the young men forced to fight it.
This film start out focusing on the friendship between Jake and Bull as much as it is on anything else, but then while hiding out from the Yankees during the winter Bull takes a liking to Sue Lee Shelly (Jewel), a young widow woman who is helping to provide them with food. Having lost both his father and his best friend, Jake continues to fight because that is what he is supposed to be doing and starts to connect with two other characters in ways that will eventually change his life. After the Lawrence Raid it is clear that the war is going to be lost and a young man who has not even seen twenty years realizes he is lost as well.
Certainly "Ride with the Devil" is a beautiful film with the sense of period authenticity you would expect from Lee. It is not really a movie about the Civil War any more than "Cold Mountain" is (an obvious comparison), but more about the friendships that take place during a war. It is just not clear that this is the central theme because our expectations are raised by more standard plot considerations (love and revenge) that do not get played out the way you would think. There is also a sense in which Roedel is the least interesting character of the bunch, yet he emerges as the central figure and the most important gun in the film is perhaps the one that is not fired.