Ride with the Devil 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 Union troops. Chiles's best 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. The two young men, used to the slow pace and gracious lifestyle of the South's privileged class, are soon confronted with the chaos of battle. Their comrades include valiant leader Black John (James Caviezel), paranoid madman Pitt (Jonathan Rhys Myers), Southern gentleman George (Simon Baker), and Daniel (Jeffrey Wright), a slave from George's plantation. The Bushwhackers hide out in a barn near the home of Sue Lee, a pregnant widow whose husband died in battle three weeks after their marriage.