November 24, 1999 | Once you get past Glory, Gone with the Wind and, arguably, Gettysburg, it’s difficult to think of many first-rate movies about the Civil War. Ride with the Devil may not rank as truly great cinema –- it tries to cover too much ground, and lacks a consistently sharp focus - – but it’s an ambitious and intelligent effort that is altogether worthy of inclusion on a very short list.

Directed with rousing vigor and meticulous precision by Ang Lee (Sense and Sensibility), Ride with the Devil also earns points for taking a refreshingly unconventional approach to constructing a historical epic. Instead of focusing on massive military clashes – the attacks and counterattacks that take up so much time in more traditional Civil War stories – Lee and long-time screenwriter James Schamus get up-close and intimate in their vividly detailed adaptation of Woe to Live On, Daniel Woodrell’s novel about the guerrilla warfare waged by pro-Southern Bushwhackers against Union sympathizers along the Kansas-Missouri border.

Taking a cue from The Godfather, Lee and Schamus begin with a lavish wedding sequence to provide exposition and introduce major characters. The year is 1861, the setting is a Missouri plantation -- and the festive mood is tempered by anxious talk of “Yankee aggressors.” (Most of that talk is of the flowery, contraction-free nature, and while it’s historically accurate, it takes a little getting used to.)

Jack Bull Chiles (Skeet Ulrich), the son of wealthy landowners, and Jake Roedel (Tobey Maguire), the Missouri-raised son of a German immigrant, are Southern gentlemen who wax eloquent while vowing to defend the Confederacy. Unfortunately, they quickly find themselves forced to back words with deeds. The childhood friends become comrades-in-arms when, shortly after the wedding, pro-Union Jayhawkers kill Jack’s father.

Joining a small unit led by the stern Black John (James Caviezel of The Thin Red Line), Jack and Jake transform themselves into full-blown Bushwhackers. Unbound by formal rules of engagement, these guerrilla warriors are lethally efficient free-lancers who often don Union uniforms to trick – and, without mercy, kill – Union soldiers and sympathizers. Jake often is deeply troubled by the frequent savagery of his colleagues. But he remains loyal to the Confederacy – and, more important, to Jack – even after Union troops slaughter many of their cohorts.

Jack and Jake join an odd couple of fellow Bushwhackers -- George Clyde (Simon Baker), a dashing young Southern gentleman, and Daniel Holt (Jeffrey Wright), George’s former slave -– in seeking wintertime refuge at a secluded hillside dugout. Sue Lee (pop singer Jewel), a beautiful war widow, provides aid and comfort for the men. So much comfort, in fact, that Jack proceeds to woo the not-so-grieving widow. (“For three weeks” she says of her dearly departed, “he was a good husband. But he didn’t last.”) When she turns up pregnant, though, it’s up to Jake to do the right thing -- whether he wants to or not –- between bloody battles for a lost cause.

Lee evidences an impressive mastery of montage as he offers many horrifically thrilling scenes of hand-to-hand combat. The early Union assault on the Bushwhacker stronghold recalls a strikingly similar police raid on a motel hideout in Bonnie and Clyde.  Later, just in time to provide a well-positioned moral turning point for Jake, William Quantrill’s infamous 1863 raid on Lawrence, Kansas – which ended with 180 dead at the hands of Quantrill and his Bushwhackers – is recreated with stunning dramatic impact.

Even more impressive, however, is the way Lee and Schamus deal with those elements of their period story that might offend contemporary sensibilities. To be blunt: Filmmakers tread on razor-thin ice whenever they romanticize Southern traditions – especially those traditions that involve slave ownership – while casting abolitionists as bad guys. (When the ice cracks, you’re left with something as ludicrous as 1940’s Santa Fe Trail, in which Errol Flynn and Ronald Reagan fight anti-slavery zealots – including John Brown himself – while taking great pains to acknowledge that slavery itself isn’t very nice.) Lee and Schamus do themselves proud by being at once honest and ambiguous, historically accurate and insightfully humane, while dealing sympathetically, but not uncritically, with the actions and attitudes of their central characters.

Oddly enough – and this is meant as an observation, not a criticism – Ride with the Devil resembles nothing so much as a World War II drama about idealistic young Germans who are bitterly disillusioned while enduring the amoral rigors of combat. That impression is repeatedly reinforced by Tobey Maguire’s strong and subtle performance as Jake, a naïve idealist whose coming of age under fire gradually emerges as the center of gravity for the movie.

In his scenes of romantic sparring with Jewel -– who is well cast and compelling in a key role -– Maguire conveys an engaging mix of pride, timidity and infatuation. But those interludes are just fleeting reminders of an irrecoverably lost innocence. Like too many other young men in too many other wars, Maguire’s Jake Roedel sees too much, and grows up too fast. And somewhere along the way, he loses faith in the very things that made him go to war in the first place.