A frustratingly not-terrible action thriller.
"Ride With the Devil" is the first Civil War film I can recall that is not told with the benefit of hindsight. It's about characters who don't know the North will win--and sometimes don't much seem to care. It's said that all politics are local; this movie argues that some wars are local, too. In Missouri, the only slave-holding state that sided with the Union, it tells the story of a small group of guerrillas with such complex personal motives that it even includes a black man who fights for the South.
The film has been made by Ang Lee, the gifted Taiwan-born, Illinois-educated director ("Sense And Sensibility," "The Ice Storm") who is able to see the Civil War from the outside. Based on a historical novel by Daniel Woodrell, the story of "Ride With the Devil" centers on southwestern Missouri, where the Missouri Irregulars, known as Bushwhackers, waged a hit-and-run fight against the Union troops, called Jayhawkers. This is basically a local war among neighbors with personal animosities and little interest in the war's ideological underpinnings.
We follow four Bushwhackers in particular: Jake Roedel (Tobey Maguire), Jack Bull Chiles (Skeet Ulrich), George Clyde (Simon Baker-Denny) and the freed black slave Daniel Holt (Jeffrey Wright). The film opens with a farm wedding they attend; later they see the farm burned and its owners murdered in a Jayhawker raid.
Roedel and Chiles want revenge. Clyde, a Southerner, believes in Dixie values and traditions, but is complex enough to have freed Holt, once his slave. Holt's motives are the most impenetrable. Why would a former slave fight for the South? He indicates it is out of personal loyalty to Clyde, who freed him and says he "trusts him with my life every day." Also perhaps because of a bond with his comrades. But Holt says little and his eyes often make a silent commentary on what he sees and hears; we wait through the film for a revelation of his deepest feelings.