Woe to live on: Ang Lee's "Ride with the Devil" at 20

Ang Lee’s “Ride with the Devil” is a tale of the Civil War told from the side of Missouri Bushwhackers, who, given their loyalty to the South (driven chiefly by their reliance on slavery), mounted a guerilla-style opposition to the encroaching Union Army — which, in this region, was largely represented by the Northern-affiliated Jayhawkers. It presents as a film about two young friends — wealthy, native-born Jack Bull Chiles (Skeet Ulrich) and poor, German-born Jake Roedel (Tobey Maguire) — fighting to preserve a dying way of life. But it gradually turns into a completely different story about two subjugated individuals — Roedel and freed slave Daniel Holt (Jeffrey Wright) — who risk their lives for their oppressors’ cause because it’s all they’ve ever known.

Lee’s follow-up to his widely acclaimed U.S. debut, "The Ice Storm," arrived in theaters during the monumental film year of 1999, and because it is awash in cognitive dissonance and bereft of razzle-dazzle technique, it failed to find favor with cinephiles drunk on the iconoclasm of "Fight Club," “The Matrix” and "Three Kings." On the surface, it looked like the anti-1999 movie; a hoary Civil War epic headlined by second and third casting choices. The Bushwhacker perspective and un-hip combination of Ulrich, Maguire and, in her feature debut (three years removed from her breakthrough single), folk-rock-singer Jewel left Barry Diller’s fledgling USA Films (a mash-up of the failed Gramercy Pictures and October Films) with nothing to sell. Factor in mixed reviews from critics, and the $38 million production wound up being most notable as one of the year’s biggest bombs.

And yet 20 years later, there isn’t a film from that year that resonates more deeply for me.

It’s a miracle “Ride with the Devil” exists at all. With the exception of “Gone with the Wind," Civil War dramas weren’t sure-fire box office successes, and Lee’s film, written by frequent collaborator James Schamus (based on Daniel Woodrell’s novel, “Woe to Live On”), dealt with a far-flung portion of the conflict that received, at best, a paragraph or two in high school history books. That it was set from a Confederacy-affiliated perspective further muddied its commercial prospects. And while Lee was an internationally renowned filmmaker at this point, he had yet to score his worldwide box-office breakthrough with "Crouching Tiger, Hidden Dragon." "Ride with the Devil" was a risk only Netflix would take today. (And Lee would probably shoot it in HFR instead of on 35mm with the great Frederick Elmes, but let’s not get into that now.)

As storytellers, Lee and Schamus are faced with an unenviable task: to orient us in this world of blurred sympathies and get us empathizing with pro-slavery Bushwhackers who toss around the n-word with total abandon. Even Roedel, a German immigrant derisively referred to as “Dutchie” by his fellow combatants, indulges in the slurring, particularly with the addition of Holt and his friend/keeper George Clyde (Simon Baker) to the company (Though Clyde bought Holt’s freedom, he’s still viewed as his “pet n***er”.) For Roedel, this is a rare opportunity to feel express social superiority over someone, and for much of the early going he resents and denigrates Holt.

This world is so underrepresented in movie history that Lee and Schamus get away scot-free with a series of opening scenes comprised of overt historical exposition. After a skillfully written introductory title card, they thrust us into the wedding of Jack Bull’s sister, which is held on his father, Asa Chiles’ (David Darlow), estate. The Criterion Collection’s “Extended Edition” expands a crucial scene wherein a Confederate sympathizer verbally spars with the Union-aligned Bowden family (including a pre-stardom Mark Ruffalo), and it is important context in that we see Asa as a well-off landowner who’s coolly unconcerned about the Union/Jayhawker incursion into Missouri. 

This dialogue would fall flat in lesser hands, but Lee and Schamus invest it with the pleasing period musicality that pervades the rest of the movie. It’s like watching a live-action rendition of Ken Burns’ “The Civil War”: You just love to hear these people talk.

The Chiles’ edenesque existence is despoiled that evening when Jayhawkers torch the house and murder Asa. Jack Bull escapes with Jake, and we fade forward to an open-air saloon where a band of Bushwhackers posing as Union men slaughter a group of unsuspecting Jayhawkers. Jack Bull and Jake are a part of this crew (led by Jim Caviezel’s Black John), and we see both characters kill in the name of the South. It’s a viscerally exciting scene — all of the violence in the film is dynamically staged — but we feel no joy or satisfaction in these killings. 

The rest of the film proceeds in this conflicted fashion. We fully understand the fury of these young men. The world they knew is now nothing more than a heap of ashes, and they’re out to inflict their wrath on every blue-jacketed bastard who helped stoke the flames. And you never once feel you’re in the company of monsters because… well, you aren’t. These kids have a pinhole view of life. The best of them have some degree of compassion for those in their company regardless of their social standing. They take care of their own. They just can’t conceive of or care for the suffering of those on the other side of the conflict because at no point in their education was it ever suggested that black people are human beings.

This is clear in the main characters’ dealings with Holt, who, despite his taciturn demeanor, is easily the most fascinating character in the film. The first time we see him, it’s in a long shot where he’s busily tending to camp as George looks on. We learn the parameters of his so-called freedom and discover that he’s killed several union soldiers in defense of George. So — as a freed slave who’s given to killing those ostensibly dying for his right to be free — he’s an especially marked man. 

Throughout the film, Jake and Jack Bull come to respect Holt for his lethality in combat, but when they make camp for the winter on a Bushwhacker-supporter’s estate, he’s still seeing to horses and basically playing the role of servant. Occasionally, Jack Bull relegates Jake to these duties, which chafes the latter at first. But the more time the two outcasts spend with each other, the more they realize they have in common.

The film’s cleverest plot twist — and it’s much more plot-driven than many critics initially realized — involves Jack Bull’s courtship of Sue Lee Shelley (Jewel), which is physically consummated on the same day he’s severely wounded in a skirmish with Jayhawkers. Jack Bull succumbs to his wounds, which forces Jake and Holt to transport Sue Lee to a safe haven. They find refuge at the homestead of Orton Brown (Tom Wilkinson underplaying as only he can) and then return to battle. Nearly a year later, a wounded Jake and Holt seek shelter at the Browns’ once more; Sue Lee is still there, as is her infant daughter. The Browns believe Jake is the father, and while they’re more than happy to let these two Bushwhackers heal up in their house (Orton is especially enamored of Holt’s handiness with a rifle), they won’t allow sin to reside there for longer than is necessary. Once Jake is recovered, Orton rustles up a minister and forces Jake to marry Sue Lee.

Lee could’ve relegated Holt to a sidekick role throughout all of this, but he never lets us forget that this is a man with a past. And now that he has his freedom (and the war is drawing to a close), he intends to ride to Texas to see about buying his mother’s freedom — if he can find her. Yes, he stays with Jake and Sue Lee until they can safely ride through Union-controlled territory, but that’s out of friendship, not servitude. 

This is the entire theme of the film; it’s a small gesture, and it sneaks up on you because it’s such a big movie. You can easily lose the forest for the trees. Jake and Holt each possess a true moral compass, but they are not conscience-stricken individuals. They mount up with William Quantrill for the infamous raid on Lawrence, Kansas, and numbly observe the massacre. They go along to get along because to do otherwise would be to die. But like many soldiers who’ve seen too much death, they never discuss the aftermath. They absorb and compartmentalize it. It will be with them forever, but survival demands that they not deal with it right this instant. 

Jake and Holt are just two young men dropped into atrocious circumstances — and you don’t realize how young until Jake gets a shave and a haircut before leaving the Browns’. Once he’s shorn of his “Bushwhacker curls” you see the baby-faced Maguire of “The Ice Storm." Orton remarks that he looks all of 21. Jake replies that he’s “just now 19.” “Is that so?” responds Orton. And your heart shatters into a million pieces.

There’s been no mention of age throughout Lee’s film until now. These aren’t young men. Jake, Holt, Jack Bull, George, Sue Lee… they’re children. Lee’s understated approach has been a quietly ticking emotional time bomb. By the time you reach the final scene, where Jake and Holt regard each other by their full names before the latter hurtles off on a horse bound for Texas, you’re left yearning for their well-earned happiness while trying like hell to forget how American history played out from that point forward. 

Person-to-person, we can make this work. As factionalized masses, we’re hostage to our hatred.