Film

Ride with the Devil

Name: Ride with the Devil
Genre: Drama, War, Romance, Western
Released: 1999
Cast: Skeet Ulrich, Tobey Maguire, Jewel, Jeffrey Wright, Simon Baker

War drama

Ang Lee's revisionist Civil War western follows Missouri guerrillas navigating duty, friendship, and moral compromise. It's a film about the grind of conflict rather than heroism—muddy, ambiguous, and preoccupied with how good men rationalize bad choices. For viewers who want their history complicated and their violence costly.

TMDb rating

3.2

Should you watch it?

Watch it if you love slow-burning frontier stories where loyalty, friendship and moral drift matter more than gunfights, and you don't mind sitting with uncertain characters.

Skip it if you want the war to be a clean backdrop for big set pieces, since this one lingers on conversations, camp life and long stretches of quiet.

What it asks of you: Nearly two and a half hours at an unhurried pace, in a grey, watchful mood that rewards patience; the payoff builds through accumulation rather than single scenes.

Not sure? Find tonight's pick in a minute.

If you liked this

The Outlaw Josey Wales1976

Clint Eastwood as a man driven by vengeance into outlaw life, finding unexpected grace through frontier justice. Another revisionist western that treats violence as consequence, not catharsis.

But It's leaner and more myth-like than Ride with the Devil; some find it dated in pacing and politics.

Cold Mountain2003

A haunted soldier's journey home during the Civil War, tracing the moral distance between the man who left and the man returning. Nicole Kidman and Jude Law anchor a film as concerned with loss as with landscape.

But Nearly three hours. The romance plot can overwhelm the historical backbone if you're here for the war, not the love story.

The Red Badge of Courage1951

John Huston's stark adaptation of Stephen Crane's novel: a young soldier's first battle seen as psychological breakdown, not glory. Black and white photography that makes everything feel like ash and doubt.

But It's slower than you'd expect and openly contemptuous of patriotic myth; that can read as bleak.

Not sure tonight? Get a pick in a minute, starting from Ride with the Devil

The wildcard

Something you would not have found on your own.

Drums Along the Mohawk1939

Both films are about the war as a catastrophe that befalls civilians trying to live, not an event to be overcome. Ford and Lee both ask what home means when home is burning.

John Ford's Revolutionary War film predates your whole conversation about revisionism. It's a home-front drama about ordinary people trying to farm while war happens, with no interest in glory or heroics. Henry Fonda and Claudette Colbert build something real from dirt and fear.

But It's eighty-four years old, Technicolor, and made when cinema was still learning to whisper. The violence is offscreen and the pacing ceremonial.

Civil War2024

A documentary-style film about war photographers moving through a fractured America. Less concerned with sides than with the cost of witnessing. Visually stunning and ethically serious.

But It arrives with minimal exposition and refuses to explain itself. That ambiguity is the point, but it demands active attention.

The Killer2023

David Fincher's study of a solitary, compartmentalized man confronting the consequences of his choices. Like Ride with the Devil, it's fascinated by how we justify ourselves when morality breaks down.

But Michael Fincher's tone is ice-cold and the pace glacial. If you want warmth or momentum, this isn't it.

Dances with Wolves1990

Kevin Costner's epic follows a Union soldier who joins the Lakota people, watching history from the perspective of those erased. Enormous in scope and asks hard questions about loyalty and belonging.

But Nearly four hours. Some find it ponderous and self-satisfied, and its portrayal of Indigenous life has aged into complications.

True Grit2010

The Coen Brothers' remake subtracts sentimentality and leaves you with a girl, a marshal, and a dead outlaw to retrieve across difficult country. Jeff Bridges and Hailee Steinfeld in a western about principle, not spectacle.

But It's spare and funny in a way that some mistake for coldness. The dialogue is period-accurate archaic.

The Civil War1991

Ken Burns' documentary series treats the war as American tragedy rather than triumph. Letters, photographs, and period music create something both intimate and sweeping.

But It's eleven hours across five episodes. Even at its best, documentary format isn't everyone's evening, and the pacing assumes you have time to sit with things.

Werckmeister Harmonies2001

Both watch as ordinary men—swept up in forces larger than themselves—realize they lack the moral architecture to resist. Both are unmerciful about complicity.

Béla Tarr's Hungarian apocalypse—two hours of slow, luminous black-and-white about a whale arriving in a small town and the chaos that follows. It's a film about collective delusion and moral collapse that could not be more different in setting, yet it shares Ride with the Devil's conviction that civilization is a thin thing.

But It is genuinely difficult. Long takes, minimal dialogue, no catharsis, and an ending that offers only darkness. Many people find it punishing.

True Grit1969

Both are obsessed with what honor costs when the world has abandoned it. Both follow men bound by oath to younger companions who test their certainties. Both understand that virtue and survival are not always the same thing.

Henry Hathaway's original, with John Wayne as an aging marshal hired by a fourteen-year-old girl to track her father's killer into Indian Territory. It's a western about principle that predates cynicism, yet somehow arrives at the same hard truths about justice and vengeance. Wayne is magnificent.

But The 1969 version has none of the Coens' bracing distance; it believes in its moral clarity in a way that can feel naive. Different register entirely—warmer, older, less ironic.