8 / 10
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.
The film was a box office failure on release. Universal did not 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, which is 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 were not 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 does not let him off the hook.
This is the most morally honest treatment of Confederate irregular warfare in American cinema. The film does not romanticize Quantrill. It does not romanticize Bloody Bill Anderson. It shows what the irregular war actually was, which was largely the murder of civilians.
For Writers
A protagonist on the morally wrong side of history can still be the story’s protagonist if the writer does not absolve them. Jake Roedel rides with murderers. He participates in atrocities. The film does not tell the audience to forgive him. The film tells the audience to understand him. The lesson is that moral complexity in protagonists does not 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 is 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 that was being fought to keep his people enslaved. The forgiveness is unearned. The film knows it is unearned. The forgiveness happens anyway because that is what real human beings do.
For Writers
A relationship that survives unforgivable circumstances is more interesting than a relationship that never had to survive anything. Jake and Holt should not be friends. By every reasonable accounting of the situation, Holt should hate Jake. They become friends anyway. The film does not justify this. It shows it. The lesson is that real human relationships are not always morally rational. People love and forgive each other for reasons that do not fit on a moral ledger. Write that.
The Ending
Jake survives the war. He marries Sue Lee, who is 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 has not been redeemed. The war is over. The country has decided what it is going to be. Jake is one of the people who lost, on the side of people who deserved to lose, and he is going on with his life.
The ending is the most honest a Civil War film has been about what defeat actually was for the men on the losing side. Most of them were not transformed. Most of them simply went on living. The film respects this.
For Writers
An ending does not need to provide moral resolution to be earned. Jake Roedel does not 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 does not 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 did not know what to do with the film. Director’s cut released later restored material the studio had cut.
The Verdict
8/10. The most morally honest American Civil War film. Jeffrey Wright is exceptional. Tobey Maguire is the right kind of weight for the central role. Ang Lee directs with patience and respect for the material. The film deserved better than its release got. Find the director’s cut if you can.
FAQ
Is it based on a novel?
Yes. Daniel Woodrell’s Woe to Live On (1987). Woodrell is from Missouri and his fiction is grounded in the region’s history.
Did free Black men really fight for the Confederacy?
A small number did, generally out of personal loyalty rather than political commitment. The historical record is complicated. Daniel Holt’s character is plausible if uncommon.
Is the Lawrence Massacre depicted accurately?
Yes. The historical massacre of approximately one hundred and fifty civilians in Lawrence, Kansas on August 21, 1863 is depicted with appropriate brutality. The film does not soften it.
Who is Jewel?
The singer-songwriter Jewel Kilcher, who acts in Ride with the Devil under her single name. She is competent in the role. It was her acting debut.
Is there a director’s cut?
Yes. The original theatrical release was about twenty minutes shorter than Lee’s preferred version. The director’s cut is the one to watch.
How does it compare to other Civil War films?
The most morally complex. Glory is the best emotionally. Lincoln is the best politically. Ride with the Devil is the most honest about what the war actually was for most of the people fighting it.
Should I watch this?
Yes. Especially if you have only seen the major mainstream Civil War films.