Based on a novel by Daniel Woodrell, Ride with the Devil is set along the Missouri-Kansas border where Bushwhackers and Jayhawkers engaged in something like terrorism--ambushes, night raids, skirmishes in the woods. And what's provocative about the movie is that it takes the Bushwhackers' point of view. The South has done just fine in Civil War movies, from Birth of a Nation to Gone with the Wind, but it's still a little creepy to see a movie waving the Confederate flag, rather like seeing a Mississippi pickup truck do the same. Lee and James Schamus (who adapted the novel) want us to see that the Civil War wasn't us-versus-them, it was us-versus-us. The filmmakers don't paint in black and white; they don't even paint in blue and gray. (Uniformed soldiers are almost not to be found.) They paint in gray...fading to black.
Tobey Maguire is Jake Roedel, a German immigrant's son who gets pulled into the conflict by his best friend, Jack Bull Chiles (Skeet Ulrich). Jack's a true believer, his father having been murdered by Jayhawkers. And Jake? Jake is Jack's best friend, so he comes along for the ride. And what a ride it is! Like a couple of outlaws, they haunt the hills of western Missouri, striking fear in the hearts of Yankee sympathizers. Lee, who's never shown much interest in action before (no car chases that I recall in Sense and Sensibility), keeps a tight rein on the gun battles, which might easily have slid into Butch and Sundance: The Early Days. And he shows a fine eye for detail. The guns, for instance, actually seem to weigh something. And the bullets, which sound like bombs when they're being fired, all but knock a man down with their impact.
After a season in the sun, Jake and Jack hole up in the woods for the winter. They're joined by Holt (Jeffrey Wright), a freed slave who, out of loyalty to his former master, fights for the South. And they receive periodic visits from Sue Lee, a young war widow played by pop star Jewel. The Young Guns casting might have been a problem if the actors weren't so deft at handling Schamus' Holy Bible-meets-Mark Twain dialogue. "It makes me notable by the loss," Jake says after he gets a finger blown off, and it's a tribute to Maguire's careful underplaying that the line seems both funny and real. All the male characters have a cowboy's reticence, the ability to talk around what they're really feeling. And the movie can be awfully funny in a way that Twain would have loved--understatement and overstatement poking each other in the ribs.
It's also strangely moving as the rag-tag group around Jake and Jack shifts and thins, then fades away. Finally, after a raid on Lawrence, Kansas--a sickening slaughter that Lee handles like a master--we zero in on Jake, Holt and Sue Lee. Jake and Holt get a Huck-and-Jim thing going, and Sue Lee, who'd been Jack's girl, takes a good strong look at Jake and wonders whether he's telling the truth when he says that marriage is akin to slavery. Speaking of slavery, some viewers may balk at the Holt character, who seems to put honor above freedom, as if it were possible to have the former without the latter. All I can say in the movie's defense is that it's about the difficult choices that were made during this difficult time, when to stand on the border between North and South was to risk losing yourself altogether.