Synopsis

During the Civil War's brutal Kansas-Missouri border conflict, German immigrant Jake Roedel joins Confederate guerrillas after his family is attacked. Fighting alongside his friend Jack Bull and the former slave Daniel Holt, Jake confronts shifting loyalties, revenge, racial divisions, and the devastating cost of war. As the group's cause collapses, friendship and survival become more important than ideology.

Factoids & Trivia

• The film is based on Daniel Woodrell's 1987 novel Woe to Live On. The book was retitled Ride with the Devil for its 1999 movie tie-in edition.

• Rather than focusing on the Civil War's major eastern battles, the story takes place during the guerrilla warfare of the Kansas-Missouri border, where allegiances were often personal and local.

• Filming took place largely in Kansas and Missouri, including locations around Kansas City, Lawrence, Lexington, and other communities near the historic border-war region.

• Daniel Holt's unusual position as a Black man fighting with pro-Confederate guerrillas was inspired by a handwritten first-person account discovered during research at the University of Kansas.

• Jewel made her feature-film debut in the picture. Her participation brought a well-known recording artist into a demanding period production rather than a contemporary musical role.

• The movie premiered at the Deauville American Film Festival on September 9, 1999, before receiving a limited U.S. theatrical release in November.

• Its original theatrical version runs 138 minutes. A 148-minute director's cut, reflecting Ang Lee's preferred version, was later restored and released by The Criterion Collection.

• The film had a modest theatrical run, earning approximately $635,000 domestically. Its later home-video and Criterion releases helped establish it as an underseen Civil War film.

• The title reflects the period's demonization of guerrilla fighters, who were frequently described as devils or demons by civilians and military observers on both sides.