Theatrical release: November 24, 1999.
Shot on location in Kansas and Missouri.
The actors went through a three-week training period, during which they learned how to ride horses, fire weapons, and speak in an authentic Southern dialect. They also ate period food such as salt pork bacon and hardtack. Several actors did not bathe or shave for a few days so as to experience the hardships the Bushwhackers faced. Director Ang Lee also assigned the actors a reading list, which included THE RED BADGE OF COURAGE by Stephen Crane, THE ADVENTURES OF HUCKLEBERRY FINN by Mark Twain, and THE DEVIL KNOWS HOW TO RIDE, a biography of the Bushwhacker William Quantrill by Edward E. Leslie.
Bad weather from El Nio often turned the film's shooting locations into muddy messes. In a reference to his previous film, Lee jokingly labeled the sets the Mud Storm.
Jewel grew up in a cabin in Alaska, so she could identify with the hardships her character, Sue Lee, faced. To memorize her lines, Jewel often sang them to herself. She also wrote several songs from the perspective of her character. One, "What's Simple Is True," is played over the film's credits.
Matt Damon was offered the part of Jack Bull, but he declined and appeared in THE TALENTED MR. RIPLEY instead. Damon's move caused Fox Searchlight to drop RIDE WITH THE DEVIL. The film was then picked up by Universal.
Revenge raids between the Bushwhackers and the Jayhawkers lasted for more than a decade after the Civil War ended.
"I grew up in Taiwan, where older people always complained that kids are becoming Americanized; they don't follow tradition, and so we are losing our culture. As I got the chance to go around a large part of the world with my films, I would hear the same complaints. It seems so much of the world is becoming Americanized. When I read Daniel Woodrell's book WOE TO LIVE ON, which we based RIDE WITH THE DEVIL on, I realized that the American Civil War was, in a way, where it all started. It was where the Yankees won not only territory but, in a sense, a victory for a whole way of life and thinking."--Ang Lee, in an interview at the RIDE WITH THE DEVIL Web site.
"When we were making SENSE AND SENSIBILITY, there was a moment when Ang turned to me and said, 'You know, some day I'd like to make a movie with characters who have dirty fingernails.' And there are lots of those in Daniel's book."--James Schamus, in an interview at the RIDE WITH THE DEVIL Web site.
"A studio executive told us, I'm not spending millions of dollars on a movie with 'woe' in the title.' So, reflecting the different needs of the medium, the novel WOE TO LIVE ON became the movie RIDE WITH THE DEVIL."--Ted Hope, in an interview at the RIDE WITH THE DEVIL Web site.