A sweeping tale of conflicted allegiances and ambiguous moralities, Ride with the Devil does justice to the complexity of the American Civil War as fought on the Missouri/Kansas border. Its large cast is lead by Tobey Maguire as Jake Roedel, the son of a German immigrant, who sides with the political views of his loyalist best friend Jack Chiles (Skeet Ulrich). Joining up with Bushwhackers commanded by Black John (Jim Caviezel), they strike back at the Union and the Union-sympathetic Jayhawkers alike. Jake will eventually find himself following the infamous William Quantrill into a massacre that leaves dead more than 200 male inhabitants of Lawrence, Kansas. However, Jake has little stomach for the warfare practiced by Quantrill and the crazed Pitt Mackseon (Jonathan Rhys Meyers). He gradually loses his belief in the South as he meets Sue Lee Shelley (Jewel), a soldier’s widow, and Daniel Holt (Jeffrey Wright), a former slave attached to George Clyde (Simon Baker), Bushwhacker and son of Holt’s former owner.
It’s little surprise that Ride with the Devil was not a financial success – it asks the viewer to conider the perspective of the war’s losing side, but it’s persistent in showing their racism and brutality. Of course, this is not at all a bad thing. This film respects the viewer’s intelligence, letting them draw their own conclusions about why each of these people fought their neighbours as well as the Union. It also offers up detailed characterisation, elegant period dialogue, lingering landscape shots, and impressive action scenes that often involve hundreds of men on horseback. For all of these reasons, the film doesn’t deserve the relative obscurity into which it has sunk.
Ride with the Devil was clearly cast in the hopes (for naught) that its lead actors would draw audiences. Some of them are much less appealing in hindsight, but though I certainly wish the cast were different, even these late 90s heartthrobs don’t bring down the movie. The younger actors aren’t bad, but they don’t bring much to their roles. They’re missing something. Maguire probably looks the part – Jake is young, impressionable and not physically imposing – but he has little presence. Meyers tries for pretty/crazy, but doesn’t have the off-kilter quality the character needs, and Ulrich is just uninteresting. As for Jewel… Well, why not? Even Ricky Nelson couldn’t ruin Rio Bravo, after all, and she doesn’t stop the movie for a song. With her imperfect teeth and round face, she doesn’t look quite like a typical starlet, either. There’s nothing at all objectionable about her performance, and I’m disappointed that she’s done little acting since.
Maybe I’ve been too hard on these younger actors – my preconceptions make me averse to all of them, particularly Maguire and Baker. However, it’s plain to see that there are better actors in this film. Zach Gremier and Mark Ruffalo convey a good deal with their little screentime. Caviezel shows the way John’s mindset shifts as the war progresses. Jeffrey Wright, meanwhile, runs away with the film. Even in his early scenes, where he doesn’t talk much, he manages to keep the viewer wondering who Holt is and what his motivations are. Watching his character unfold, and make his choices, is the most moving aspect of this story.
Ride with the Devil would be better with a less of-the-moment cast. However, neither its lead actors, nor audiences’ disinterest upon the film’s initial release, are indicators of how rewarding it is as a nuanced presentation of history.