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Ang Lee fought an unconventional Civil War battle with this 1999 flop

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One week a month, Watch This offers movie recommendations inspired by the week’s new releases or premieres. This week: Free State Of Jones looks back on the Civil War (no, not that one), so we look back on earlier Civil War movies.

Ride With The Devil (1999)

Ang Lee has a way of looking at U.S. history and culture with fresh eyes, making familiar touchstones feel new. Though Brokeback Mountain, Taking Woodstock, and The Ice Storm train his outsider’s eye on the ’60s and ’70s, his less-heralded Ride With The Devil (sandwiched between Ice Storm and Crouching Tiger, Hidden Dragon on his filmography) goes another century back for a Civil War story. Lee’s film, based on the book Woe To Live On by Daniel Woodrell, doesn’t focus on that conflict’s most famous watershed moments. It takes place off in Missouri, where close friends Jake (Tobey Maguire) and Jack (Skeet Ulrich) join up with the Bushwhackers, a Confederate-affiliated group of guerrilla fighters, after the Union-affiliated Jayhawkers murder Jack’s father. They ride with Holt (Jeffrey Wright), a former slave fighting alongside the Bushwhacker who has freed him.


Instead of epic battlefield clashes, the action is often claustrophobic and ragged, like a shoot-out at a small homestead where the Bushwhackers are holed up, or another, even more chaotic gunfight that takes place in an open clearing with almost no cover for anyone. The guerrilla fighting also means plenty of downtime, including a “hibernation” for the winter months in a home base dug out of a hill. In between episodes of carnage, Lee often sets his scenes with painterly multi-character tableaux. He has plenty of compelling actors to arrange: In addition to a pre-Spider Man Maguire, the movie features a pre-Jesus Jim Caviezel, a pre-You Can Count On Me Mark Ruffalo, a pre-Justified Margo Martindale, and a pre-Mentalist Simon Baker.

This is a leisurely and sometimes emotionally muted war story, but it provides space to explore Civil War territory not always covered in similar films. Sometimes Lee and screenwriter/frequent collaborator James Schamus reverse the old saw about the war’s conflicts necessitating personal divisions, as when as when Jake’s father is murdered offscreen not for his side in the war (he’s on the same side as his killer) but because he’s part of Jake’s family. This foreshadows the war’s endgame; by just past the movie’s halfway mark, the conflict has further devolved into a series of bloody vendettas. The final stretch of Ride With The Devil captures the feeling of a war winding down (the final half-hour is one of its least action-filled sections) and, as such, the lingering resentments that made the Civil War’s wounds particularly difficult to heal.


It’s especially tricky to deal with Confederate characters who don’t seem that invested in the cause of slavery, and even count a former slave among their ranks, without delving into broader revisionism. But Wright’s performance makes it work more often than not. It’s easy to see why Ride With The Devil flopped in its initial 1999 release; it doesn’t offer much in the way of catharsis or payoff. But it’s worth seeking out for adventurous viewers, especially the version available on Blu-ray from Criterion, which is the 10-minutes-longer director’s cut. The Criterion release places this flawed but interesting movie in the context of a notable filmmaker’s career.

Availability: In addition to the Criterion disc, Ride With The Devil is available in its theatrical form on disc through Netflix or possibly your local video store/library. It can also be rented or purchased through the major digital services.