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Ride with the Devil

Ride with the Devil is a 1999 American revisionist Western film directed by Ang Lee, and starring Tobey Maguire, Skeet Ulrich, Jeffrey Wright, and Jewel in her feature film debut. Based on the novel Woe to Live On, by Daniel Woodrell, the film, set during the American Civil War, follows a group of men who join the First Missouri Irregulars, also known as the Bushwhackers—guerrilla units loyal to pro-Confederacy units of the state—and their attempt to disrupt and marginalize the political activities of Northern Jayhawkers allied with Union soldiers. Simon Baker, Jonathan Rhys Meyers, Jonathan Brandis, Jim Caviezel, Mark Ruffalo, and Celia Weston are featured in supporting performances.

Plot

Jake Roedel and Jack Bull Chiles are friends in Missouri when the American Civil War breaks out. During the mayhem, Chiles' father is murdered by Kansas pro-Union Jayhawkers. The two men join the First Missouri Irregulars (Bushwhackers) under Black John Ambrose, an informal unit loyal to pro-Confederacy units of Missouri in 1861. They later meet George Clyde and his slave Daniel Holt, who is serving in the Irregulars as Clyde's additional fighter. Having been trained in fire arms, and proven a good shot who is cool in combat, Holt is known as a good Yankee killer.