8 / 10
Official trailer
Ride with the Devil is Ang Lee’s overlooked Civil War film.
James Schamus wrote the screenplay, adapted from Daniel Woodrell’s novel Woe to Live On. Tobey Maguire plays Jake Roedel, the son of a German immigrant in western Missouri who joins a Confederate guerrilla band more out of loyalty to his friends than out of political conviction. Skeet Ulrich plays Jack Bull Chiles, his best friend. Jeffrey Wright plays Daniel Holt, a freed slave who rides with the Confederate irregulars for reasons the film takes time to explore.
Jewel Kilcher (just Jewel) plays Sue Lee Shelley in her acting debut.
Ang Lee made a Civil War film that almost nobody saw, and I think it’s among his best work. He looks at the ugliest corner of that war, the guerrilla killing along the Missouri-Kansas border, and refuses to make anybody a hero, including the boy we follow.
Jeffrey Wright is the best thing in it. My reservation is pace. Lee’s patience serves the film most of the way, and in the middle stretches it turns into drift.
The film was a box office failure on release.
Universal didn’t know how to market it. Critics were mixed. Twenty-five years later, the reputation has shifted significantly upward. The film addresses an aspect of the Civil War that mainstream cinema avoided, the brutal irregular fighting along the Missouri-Kansas border, including Quantrill’s Raiders and the Lawrence Massacre of August 1863.
The Bushwhackers
The Missouri Bushwhackers weren’t Confederate regulars. They were guerrilla fighters operating outside conventional military structure, often outside conventional military ethics.
The Lawrence Massacre, in which William Quantrill’s men murdered approximately one hundred and fifty Kansas civilians, mostly men and boys, is the most infamous incident of the irregular war. The film stages it without flinching. Jake participates. Jake watches Bushwhackers shoot teenage boys in front of their mothers. The film doesn’t let him off the hook.
I think this is the most morally honest treatment of Confederate irregular warfare American cinema has produced. The film doesn’t romanticize Quantrill or Bloody Bill Anderson, and it shows the irregular war for what it largely was, the murder of civilians. The Lawrence sequence made me feel sick, and I respect the film enormously for putting its own protagonist in the middle of it.
For Writers
A protagonist on the morally wrong side of history can still be the story’s protagonist if the writer doesn’t absolve them. Jake Roedel rides with murderers and participates in atrocities. The film doesn’t tell the audience to forgive him. It tells the audience to understand him. The lesson is that moral complexity in protagonists doesn’t require redemption. It requires honesty. Show the character making the choices. Let the reader judge.
Daniel Holt
Jeffrey Wright’s Daniel Holt is the film’s secret weapon.
Holt is a freed Black man riding with Confederate guerrillas because the man who freed him is among them and Holt is loyal to him. The historical situation existed. Some free Blacks did fight for the Confederacy, generally out of personal loyalty to specific white men, generally without any commitment to the Confederate cause. The film is the only American mainstream film to address this dynamic seriously.
Wright plays Holt as a man who’s on the wrong side of his own war and knows it.
The friendship that develops between Jake and Holt is the moral center of the film. By the end of the film, Holt has effectively forgiven Jake for participating in a war the South was fighting to keep his people enslaved. The forgiveness is unearned. The film knows it’s unearned. The forgiveness happens anyway because that’s what real human beings do.
Wright is the reason I’d tell anybody to seek this out. He plays Holt with so much held back that every silence tells you he knows exactly what side he’s riding with. That forgiveness should feel false, and in his hands I believe it completely.
For Writers
A relationship that survives unforgivable circumstances is more interesting than a relationship that never had to survive anything. Jake and Holt shouldn’t be friends. By every reasonable accounting of the situation, Holt should hate Jake. They become friends anyway. The film doesn’t justify this. It shows it. The lesson is that real human relationships aren’t always morally rational. People love and forgive each other for reasons that don’t fit on a moral ledger. Write that.
The Ending
Jake survives the war. He marries Sue Lee, who’s pregnant with the dead Jack Bull’s child. He rides west with Holt, looking for Holt’s mother in Texas. The final scenes are quiet and unresolved.
Jake hasn’t been redeemed. The war is over. The country has decided what it’s going to be. Jake is one of the people who lost, on the side of people who deserved to lose, and he’s going on with his life.
The ending is the most honest a Civil War film has been about what defeat was for the men on the losing side. Most of them weren’t transformed. Most of them simply went on living. The film respects this.
The ending is my favorite thing in the film after Wright. Lee lets Jake ride away without a speech or a redemption scene. He heads west with Holt, a married man with a war behind him that he fought on the wrong side, and I found that quiet close braver than any big finale would have been.
For Writers
An ending doesn’t need to provide moral resolution to be earned. Jake Roedel doesn’t learn his lesson. He simply survives the war and goes on with his life. The reader supplies the moral weight. The lesson is that endings that refuse to resolve the moral dimension often have more lasting power than endings that wrap the moral lesson in a bow. Real life doesn’t provide moral catharsis. Fiction that admits this is closer to honest.
Craft Note
Ang Lee directed. James Schamus adapted Daniel Woodrell’s novel Woe to Live On. Tobey Maguire as Jake Roedel. Skeet Ulrich as Jack Bull Chiles. Jeffrey Wright as Daniel Holt. Jewel (acting debut) as Sue Lee Shelley. Simon Baker as George Clyde. Mark Ruffalo, Jonathan Rhys Meyers, and Jonathan Brandis in support. Released November 1999. Approximately thirty-five million dollar budget. Approximately seven hundred and fifty thousand dollar opening weekend. Universal’s marketing department didn’t know what to do with the film. Director’s cut released later restored material the studio had cut.
Is Ride with the Devil worth watching?
My 8 comes from how honest this film is about a war most movies prefer to decorate. Wright is the standout, Tobey Maguire carries the right kind of weight in the lead, and Ang Lee treats the material with patience and respect. The drifting middle keeps it from going higher for me. It deserved far better than the release it got, so find the director’s cut if you can.
