Ride with the Devil (1999)

Directed by Ang Lee and starring Tobey Maguire and Jeffrey Wright, this film follows Jake Roedel and Jack Bull Chiles, who join the Missouri Bushwhackers following the murder of Jack Bull's father at the hands of Union soldiers. Driven by revenge, they forge a bond with a former slave named Daniel Holt, while exploring the meaning of loyalty and honor in the Civil War.