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A complex tale of uneasy alliances and hostilities along the Kansas/Missouri border during the Civil War, Ride with the Devil opens in 1862. The story concerns Jack Bull Chiles (Skeet Ulrich), a proud son of the South ready to fight for the Confederate cause after his father is killed by Yankee troops. Chiles's friend, Jake Roedel (Tobey Maguire), joins the Bushwhackers, a group of renegade Southerners aligned with the Confederate Army, even though his family supports the Union cause - which sets him head-to-head with his father. The two young men, used to the slow pace and gracious lifestyle of the South's privileged class, become guerilla fighters and wander through the countryside together, encountering sudden, shocking and extreme acts of violence. Their comrades include valiant leader Black John (James Caviezel), paranoid madman Pitt (Jonathan Rhys Myers), gentleman George (Simon Baker), and Daniel (Jeffrey Wright), a laconic former slave who unexpectedly fighs for the south despite his race out of sheer loyalty to George - though the others regard him with suspicion. The Bushwhackers hide out in a shed near the home of Sue Lee Shelley (singer/songwriter/poet Jewel), a pregnant widow whose husband was killed three weeks after their marriage. Later, following a shocking and unexpected act of violence, a number of the men team up with the crazed Quantrill (John Ales) to stage an attack on an abolitionist stronghold, but Jake finds his moral conscience growing more acute, and takes the first steps toward romancing and starting a family with Sue Lee in what looks to be a very different post-Civil War future. Adapted from the novel Woe to Live On by Daniel Woodrell, Ride with the Devil was directed by Ang Lee, whose previous project was a very different look at America's past, the 1970s domestic drama The Ice Storm (1997).