Ride with the Devil poster

Ride with the Devil

"In a No-man's Land between North and South, You didn't fight for the Blue or the Grey... You fought for your friends and family."

Movie R 1999 2h 18m 6.3 /10
Directed by Ang Lee

On the Kansas Missouri border during the Civil War, Ride with the Devil tracks four people trying to stay true in a landscape where loyalties shift and violence rules. An ardent Unionist, a son of an immigrant, a freed enslaved person, and a young widow forge an uneasy bond as they struggle to... Read more

Watch Now

Where to Watch "Ride with the Devil"

Rent or Buy

Netflix
Amazon Prime Video
Disney+
Max
Hulu
Paramount+
Peacock
Apple TV+

Streaming availability last verified: January 22, 2026

About Ride with the Devil

On the Kansas Missouri border during the Civil War, Ride with the Devil tracks four people trying to stay true in a landscape where loyalties shift and violence rules. An ardent Unionist, a son of an immigrant, a freed enslaved person, and a young widow forge an uneasy bond as they struggle to survive. They dodge raiders, weigh risky alliances, and question what counts as honor when the law vanishes and cruelty becomes ordinary. The story narrows its focus to intimate choices and fragile friendships, honoring personal codes in a setting that feels lawless rather than heroic. Ang Lee builds a quiet, character driven drama that sits between war movie tropes and Western romance. Their fates feel personal as the war rages around them.

Directed by Ang Lee and released in 1999, Ride with the Devil presents Daniel Woodrell's material adapted for the screen by James Schamus. The production blends war realism with Western mood, anchored by Skeet Ulrich and Tobey Maguire.

The film did not garner major award nominations, reflecting its modest reception despite a high profile director and strong cast. A few critics praised its mood and performances, but overall it was seen as a minor, contemplative entry in Ang Lee's diverse body of work.

Ride with the Devil stands out for its attempt to fuse Civil War era grit with a Western romance on the border between Kansas and Missouri. Jeffrey Wright's portrayal adds gravity as a freed man, and the film foregrounds loyalty and race in unfamiliar terrain for some viewers seeking depth.

Critics treated the film as a moody, character driven drama rather than a war movie. It probes how unlikely kinships form under pressure, questions bravado, and shows violence as a shaping force on people who must choose where their loyalties lie in a landscape that tests trust and love alike.

Details

Release Date
November 24, 1999
Runtime
2h 18m
Rating
R
User Ratings
199 votes
Type
Movie
Genres
Drama, War, Romance, Western
Country
United States
Studio
Good Machine +1 more
Budget
$35,000,000
Box Office
$635,096
External Links
View on IMDB

Official Trailer

Cast

Skeet Ulrich

Skeet Ulrich

Jack Bull Chiles

Tobey Maguire

Tobey Maguire

Jake Roedel

Jewel

Jewel

Sue Lee Shelley

Jeffrey Wright

Jeffrey Wright

Daniel Holt

Simon Baker

Simon Baker

George Clyde

Jonathan Rhys Meyers

Jonathan Rhys Meyers

Pitt Mackeson

Tom Wilkinson

Tom Wilkinson

Orton Brown

Jim Caviezel

Jim Caviezel

Black John

Tom Guiry

Tom Guiry

Riley Crawford

Jonathan Brandis

Jonathan Brandis

Cave Wyatt

Director: Ang Lee

Written by: Daniel Woodrell, James Schamus

Frequently Asked Questions

Ride with the Devil is not currently available on streaming subscription services, but you can rent or buy it on Apple iTunes, Google Play, Vudu, and Amazon Video.

Yes, you can rent on Apple iTunes, Google Play, Vudu, and Amazon Video or buy on Apple iTunes, Google Play, Vudu, and Amazon Video.

With a rating of 6.3/10 from 199 viewers, Ride with the Devil is considered decent by viewers and may be worth checking out.

On the Kansas Missouri border during the Civil War, Ride with the Devil tracks four people trying to stay true in a landscape where loyalties shift and violence rules. An ardent Unionist, a son of an immigrant, a freed enslaved person, and a young widow forge an uneasy bond as they struggle to su...

Ride with the Devil stars Skeet Ulrich, Tobey Maguire, Jewel, Jeffrey Wright, and Simon Baker.

Ride with the Devil was directed by Ang Lee.

Ride with the Devil was released on November 24, 1999.

Ride with the Devil is a Drama, War, Romance, and Western film.

Tobey Maguire plays Jake Roedel, one of the four central characters. He teams up with the others to navigate life on the Missouri/Kansas border during the Civil War.

Skeet Ulrich plays Jack Bull Chiles, one of the four central characters. He is part of the group seeking truth and justice in the uncertain Civil War era.

Yes, it combines drama, war, romance and Western elements. The story unfolds on the Missouri/Kansas border during the Civil War, giving it a Western feel.

Ride with the Devil is rated R, so it's intended for adult audiences. It was directed by Ang Lee and released in 1999.