Ride With the Devil (2000)

On the fringes of the Civil War, Missouri Bushwackers engage in guerrilla warfare with Union Jayhawkers. Bushwackers Jake Roedel (Tobey Maguire) and Jack Chiles (Skeet Ulrich), out to avenge the murder of Jack's father, are joined by George Clyde (Simon Baker) and his former slave, Daniel (Jeffrey Wright). Hiding out for the winter, Jack has a short romance with a war widow (Jewel) before dying. Jake steps in to take care of her and her newborn before joining Quantrill's famous Kansas raid.