The Civil War of battlefields and plantation houses is nowhere to be seen here. Instead we see the war as an improvised and largely blundering but very bloody feud among neighbors in the border state of Missouri. In this bucolic war zone--more than a little reminiscent of the Balkans in the late 1990s--the Taiwanese-born director Ang Lee (Sense and Sensibility) traces the destinies of several young Southern bushwhackers (guerrilla fighters) as they experience violence, the seasons, and different kinds of love. Skeet Ulrich draws the aristocratic glamour role (and top billing), but he's overshadowed by Tobey Maguire as a first-generation American, the magnificent Jeffrey Wright (a shameful oversight at Oscar time) as a freed slave fighting beside his former master, and singer Jewel in a very natural acting debut as the young widow who graces all their lives. The title The Birth of a Nation was already taken, but by the end of this movie you feel it would have applied here. -- Richard T. Jameson
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.