Exclusive: Jeffrey Wright reminisces about Ang Lee's Ride with the Devil, one of the best experiences of his career -- and why the studio then swept it under the rug.
Sometimes it takes an outsider to diagnose a dysfunction in a family or the problem in a marriage. And when it comes to understanding the dynamics of the American Civil War, few filmmakers have captured the complexity and psychology that perpetuated this 19th century reckoning better than Taiwanese filmmaker Ang Lee. The director's pensive and elegiac Ride with the Devil, adapted from Woe to Live On by Daniel Woodrell, gives a thoughtful and full portrait of the "border wars" fought between neighbors in Missouri. This includes the film's tact of slowly but assuredly taking on the point of view of Jeffrey Wright's Daniel Holt, a Black man who found himself riding with Missouri Bushwhackers, Confederate sympathizers who infamously raided the town of Lawrence, Kansas.
It's a rich, layered, and even action-packed work, and yet there is a decent chance you've never heard of it, much less seen it. That strong probability remains one of the most frustrating memories in Jeffrey Wright's career.
"I love that movie," Wright says during a recent conversation about his latest project Highest 2 Lowest. "It's like the neglected stepchild of my career in some ways, because I think it's such a beautiful film and just grossly underappreciated. That had to do with the way it was released in that it kind of wasn't released."
Technically distributed into fewer than 65 theaters at the end of 1999, five years after Lee made a splash in the West's prestige space via the masterful Jane Austen adaptation, Sense & Sensibility, and one year before he helmed an Oscar-winning blockbuster in Crouching Tiger, Hidden Dragon, Ride with the Devil was an intentionally thorny film told from the vantage of both the losing side of the Civil War, as well as a Black man who actually rode with rebels like Tobey Maguire's main character Jake Roedel, and enslavers like Simon Baker's George Clyde. It is in fact Clyde's childhood friendship with Holt that creates a fascinating space of clouded loyalties and (eventual) self-emancipation.