Ang Lee is a bit of a shapeshifter. Honestly, if you look at his filmography, it feels like the work of five different people. You’ve got the martial arts mastery of Crouching Tiger, Hidden Dragon, the suburban malaise of The Ice Storm, and the heartbreaking intimacy of Brokeback Mountain. But tucked away in 1999—sandwiched between his indie successes and his global superstardom—is a movie that almost killed his momentum. Ride with the Devil director Ang Lee took a massive gamble on a Civil War story that didn't feature a single major battle at Gettysburg or a speech by Lincoln.
It bombed. Hard.
The movie earned less than $1 million at the domestic box office against a budget that hovered around $38 million. Critics at the time were... confused. They expected a sweeping epic. What they got was a gritty, morally ambiguous character study about teenage guerillas in Missouri. It was dirty. It was linguistically dense. It was basically the "anti-Titanic."
But here’s the thing: time has been incredibly kind to this film.
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The Unconventional Vision of Ride with the Devil Director Ang Lee
Most American directors approach the Civil War with a specific kind of reverence. It’s usually about the "Great Men" or the "Great Cause." Lee, coming from Taiwan, didn't have those internal biases. He looked at the American West during the 1860s and saw something that looked a lot more like the fractured, ethnic conflicts he understood from global history. He wasn't interested in the front lines. He wanted to see the "Bushwhackers"—the irregular Southern sympathizers who fought a nasty, neighbor-versus-neighbor shadow war in Missouri and Kansas.
He hired James Schamus to adapt Daniel Woodrell’s novel Woe to Live On. If you’ve ever read Woodrell (who also wrote Winter's Bone), you know his prose is like iron. It’s hard and unforgiving. Lee captured that perfectly.
The casting was a weird, brilliant risk. You had Tobey Maguire before he was Peter Parker. You had Skeet Ulrich when he was still a heartthrob. You even had Jewel—yes, the "You Were Meant for Me" singer—making her acting debut. It shouldn't have worked. Yet, Lee’s direction forced these young actors to inhabit a world where they spoke in a formal, 19th-century dialect that feels almost Shakespearean today.
People often ask why a director known for Sense and Sensibility would want to film a scene where a man’s ear gets cut off and kept as a souvenir. The answer is simple. Lee is obsessed with the idea of the "outsider." In Ride with the Devil, he focuses on Jake Roedel (Maguire), a son of German immigrants fighting for a South that doesn't really want him, and Daniel Holt (Jeffrey Wright), an enslaved man fighting alongside the very people who claim to own him.
It's complicated. It's messy. It’s exactly what 1999 audiences weren't ready for.
Why the Lawrence Massacre Scene Still Haunts Viewers
If you talk to any film student about Ride with the Devil director Ang Lee, they will eventually bring up the Lawrence Massacre. This is the centerpiece of the film. It depicts the real-life raid on Lawrence, Kansas, led by William Quantrill.
Lee doesn't film it like an action sequence. There's no soaring music.
Instead, it’s a chaotic, sickening descent into madness. We see young men, fueled by whiskey and a vague sense of vengeance, murdering civilians in their nightshirts. Lee focuses on the faces. He wants you to see the transition from "soldier" to "murderer." It’s one of the most honest depictions of war crimes ever put on celluloid.
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The technical precision here is staggering. Lee used hundreds of extras and practical effects to recreate the burning of the town. But the brilliance isn't in the fire; it's in the silence that follows. The way the smoke hangs over the charred remains of a community.
Critics like Roger Ebert eventually came around to the film's brilliance, but by then, it had already vanished from theaters. USA Films, the distributor, didn't know how to market a "Western" that was actually a deconstruction of the American myth. They tried to sell it as a romance. They tried to sell it as an adventure. It was neither. It was a tragedy about the loss of innocence in a country tearing itself apart.
The Jeffrey Wright Factor and the Complexity of Holt
We need to talk about Jeffrey Wright. Before he was in Westworld or The Batman, he gave one of the most nuanced performances of the 90s in this film.
His character, Daniel Holt, is the soul of the movie. A lot of directors would have made Holt a secondary character—a "helper" for the white protagonist. Lee doesn't do that. Holt is a man navigating an impossible situation with a level of dignity that makes the "heroes" look like children.
The relationship between Holt and Simon Baker’s character (George Clyde) is based on a strange, tragic loyalty. When Clyde dies, Holt is finally "free," but he’s in the middle of a war zone where his skin color makes him a target for both sides.
The scene where Holt explains his "black skin" to Maguire’s character is a masterclass in screenwriting and direction. It’s subtle. There’s no shouting. Just two men in a forest, realizing they are both fighting for a ghost.
A Career Nearly Derailed by a "Flop"
It's wild to think that if Crouching Tiger, Hidden Dragon hadn't been a massive hit a year later, we might not talk about Ride with the Devil director Ang Lee in the same way. The failure of Ride was a heavy blow. Lee has admitted in interviews that he felt he had failed the material and the actors.
But look at what he learned.
You can see the DNA of Ride with the Devil in almost everything he did afterward. The repressed emotions of Brokeback Mountain? That started with Jake Roedel’s inability to express his grief. The visual storytelling of Life of Pi? That was forged in the rugged landscapes of the Missouri woods.
The film also served as a training ground for a massive amount of talent.
- Tobey Maguire proved he could carry a heavy, dramatic lead.
- Mark Ruffalo has a small, early role that shows flashes of his future greatness.
- Jonathan Rhys Meyers plays a psychopathic bushwhacker with terrifying intensity.
The Criterion Collection's Rescue Mission
For years, if you wanted to see this movie, you had to find a grainy DVD in a bargain bin. It was a forgotten relic. Then, the Criterion Collection stepped in.
They released a restored version that finally did justice to Frederick Elmes’ cinematography. The colors are muted—lots of browns, greys, and deep forest greens—which perfectly mirrors the "grey area" of the morality on screen. The restoration also included a director's cut that restored some of the pacing Lee originally intended.
Watching it now, in an era where we are once again obsessed with the divisions in American society, the movie feels terrifyingly relevant. It’s a reminder that civil wars aren't fought by politicians on maps; they are fought by kids in the woods who think they're doing the right thing until they're covered in their friend's blood.
Actionable Steps for Exploring Ang Lee’s Work
If you’re looking to dive deeper into this specific era of filmmaking or understand why this movie matters now, here is how you should approach it:
- Watch the Criterion Director’s Cut: Do not watch the theatrical version if you can help it. The pacing in the 148-minute cut allows the relationships to breathe and makes the final act much more impactful.
- Read "Woe to Live On" by Daniel Woodrell: It’s a short, brutal read. Comparing the book to Lee’s film shows you exactly what he chose to emphasize—specifically the theme of finding a "chosen family" when your biological one is gone.
- Track the "Outsider" Trilogy: Watch The Ice Storm, Ride with the Devil, and Brokeback Mountain back-to-back. You’ll see a director grappling with the American identity from three completely different angles. It’s the best way to understand Lee’s specific genius.
- Listen to the Score: Mychael Danna’s music for this film is underrated. It uses period-accurate instruments but treats them with a modern, melancholic sensibility. It's great for understanding how sound design can elevate a historical drama.
- Look for the Missouri/Kansas History: If you're a history buff, look up the "Border War" or "Bleeding Kansas." The movie is surprisingly accurate about the specific political tensions of that region, which were very different from the Virginia or Georgia campaigns most people know.
Ang Lee didn't make a "Civil War movie." He made a movie about the end of childhood and the beginning of a very long, very complicated American story. It’s time we gave it the credit it deserves.