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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, Jewel in her feature film debut, Simon Baker, Jonathan Rhys Meyers, James Caviezel, Thomas Guiry and Jonathan Brandis. 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 war against Northern Jayhawkers allied with the Union army.

Plot

Jake Roedel and Jack Bull Chiles are friends in Lexington, Missouri when the Civil War breaks out (April 1861). Chiles' family are wealthy planters, and Jake's father, a German immigrant, warns him of anti-German suspicion from other Southerners. Jayhawkers set fire to the Chiles' plantation and execute Jack's father, but Jack escapes with Jake.