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Ride with the Devil is a 1999 American Revisionist Western film directed by Ang Lee.

Plot[]

Jake Roedel and Jack Bull Chiles are friends in Lexington, Missouri when the Civil War breaks out (April 1861). Chiles' family are wealthy planters, and Jake's father, a German immigrant, warns him of anti-German suspicion from other Southerners. Jayhawkers set fire to the Chiles' plantation and execute Jack's father, but Jack escapes with Jake.

One year later, they have joined the First Missouri Irregulars under "Black" John Ambrose, an informal unit loyal to the Confederate government of Missouri, alongside George Clyde, former slave Holt, and sadistic Pitt Mackeson, who despises the literate Jake. The Irregulars use guerrilla warfare against the Jayhawkers, supported by pro-Confederate citizens of Missouri. Jake spares captured Unionist Alf Bowden, his former neighbor, but news later arrives that Alf has killed Jake's father as revenge against the Irregulars.

Jake, Jack, Holt, and Clyde are sent to hide over winter, in a dugout on the property of the Evans family. A young widow in the household, Sue Lee Shelley Evans, becomes romantically involved with Jack, while Clyde leaves to romance Juanita Willard nearby. Jake bonds with Holt over captured letters, who reveals that his given name is Daniel and that Clyde, his childhood friend, bought him his freedom. An attack by Jayhawkers leaves the Evans' home burned, patriarch dead and Jack severely wounded. Clyde abandons them (supposedly to find a doctor) to rejoin the Irregulars and Captain Purdees. Jake, Holt, and Sue Lee try to amputate Jack's injured arm, but he dies from complications of gangrene.

Jake and Holt escort Shelley to the Brown family (Cave Wyatt's people) homestead before riding to find Clyde and the Irregulars. They learn the Union army has hunted down many of their comrades. The Irregulars join forces with guerrillas led by William Quantrill, who plans to raid Lawrence, Kansas. On August 21, 1863, the pro-South forces easily overcome the small garrison of troops guarding Lawrence, burn and loot shops and homes, and kill Union supporters and black freedmen. Avoiding the bloodshed, Jake and Holt find a nearby restaurant to eat breakfast, where they are threatened by Mackeson and force him to leave at gunpoint.

As the guerrillas make their escape, Ambrose accuses Jake of abandoning the Southern cause, and Union troops pursue them into the woods. Quantrill and Ambrose organize the men to feign retreat and form battle lines, holding off the pursuit. Mackeson shoots at Jake, and Holt is hit trying to return fire. Clyde rushes to his aid, but is shot through the throat and dies in Holt's arms. Wounded, Jake and Holt flee with their comrade Cave Wyatt and recuperate with the Brown family, while Sue Lee has given birth to Jack's daughter, who she calls Grace Shelley Chiles. Assuming Jake is the father, Cave urges him to marry her.

With Jack and Clyde gone, Jake and Holt reflect on their futures; Jake admits he does not want to rejoin the Irregulars and feels the war is turning against the Confederacy, while Holt confides that although he was not Clyde's slave, he feels "free" now his friend is gone. News arrives that Quantrill has fled to Kentucky and the surviving Irregulars are now outlaws, including Mackeson, who intends to settle the score with Jake. Once his guests are recovered, Mr. Brown brings home a minister, Reverend Horace Right, and the reluctant Jake is pressed into marrying Sue Lee, but comes to care for her and her child. Striking out for California with his new family, Jake (now 19 years old) cuts his hair, which he had sworn not to do until he was finished with the war.

Along the journey, Jake and Holt encounter Mackeson, who is on the run with another surviving Irregular after the executions of Ambrose and Quantrill. The outlaws are prepared to ride into Mackeson's Union-occupied hometown of Newport, Missouri, even though this means certain death. Mackeson accepts a cup of brewed chicory, but his unhinged manners lead Jake and Holt to draw their guns, and he rides off. Holt eventually parts ways with Jake while Sue Lee and the baby sleep, hoping to free his mother from slavery in Texas, and the two friends shake hands and exchange farewells.

Cast[]

  • Tobey Maguire as Jake Roedel
  • Skeet Ulrich as Jack Bull Chiles
  • Jewel as Sue Lee Shelley
  • Jeffrey Wright as Daniel Holt
  • Simon Baker as George Clyde
  • Jonathan Rhys Meyers as Pitt Mackeson
  • Jim Caviezel as Black John Ambrose
  • Tom Guiry as Riley Crawford
  • Jonathan Brandis as Cave Wyatt
  • Mark Ruffalo as Alf Bowden
  • Tom Wilkinson as Orton Brown
  • Margo Martindale as Wilma Brown
  • John Ales as William Quantrill
  • Matthew Faber as Turner Rawls
  • Celia Weston as Mrs. Clark
  • John Judd as Otto Roedel
  • Don Shanks as George
  • John Durbin as Skaggs
  • Zach Grenier as Mr. Evans
  • Stephen Mailer as Babe Hudspeth
  • James Urbaniak and David Rees Snell as poker players
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