Originally Posted by oildude
My response to the same question asked during the November 2014 B&N sale:
I think Ride with the Devil is a great film, with outstanding performances and beautiful cinematography that manages to make an unsettling tale a work of cinematic poetry. The story revolves around mounted guerrillas in the Missouri borderlands during the American Civil War, and is one of the best movies I have seen at bringing a time-period into my living room through effective use of drama, dialogue, character development, and selective use of violence. Ang Lee and the film's writers do an exceptional job of capturing the particular viciousness of this local conflict, where former neighbors and friends turned on each other with unspeakable savagery. The attention to accurate period detail is superb, and through a combination of all of the above the audience has no problem understanding how, after the war, the lingering bitterness and the prevalence of irregular guerrilla action throughout the region could give rise to the James-Younger gangs and the sympathies the locals had for them (which is why it took so many years for these gangs to finally be run to ground). The fact that this was a backwater conflict of the American Civil War, making no difference at all to the larger outcome, did not matter to the individuals engaged. To them, their fight to control territory was as real and meaningful as the battles being fought by the big armies far to the east. With the benefit of hindsight, this is the real tragedy of this whole rotten episode in American history.
The film does many things well, and in ways the viewer might not expect. For instance, how it touches on the issue of slavery and racism from a local and individual perspective. Much of this centers around Jeffrey Wright, who is magnificent in his portrayal of a slave owned by one of the guerrilla officers. Wright is as equally committed to the Southern cause as his master; he turns out to be a first-class fighter and an individual whose strength of character is greater than those around him. This creates tensions among some of the Southerners. He is one of the most intriguing and well-written characters ever to appear in a film, not least because he exists completely in his time frame, beyond the understanding of a modern audience who may have difficulty accepting his motives or viewing him as more than a historical oddity or mere contrivance in the context of the plot.
The film gets it right in portraying the torn loyalties of recent European immigrant settlers in the Missouri-Kansas region. In the years immediately prior to the Civil War, large numbers of Irish and German immigrants came to the U.S. Most settled in the northern states, where many consequently volunteered or were conscripted into the Union armies. This fact is known to the characters in the film. Tobey McGuire is very good here in his portrayal of a young Southerner born in Germany and brought to the U.S. as a baby who fights for the South because that is where his parents settled and raised him. He portrays a mildly conflicted individual with a high sense of morality who questions the madness of war and the racism shown toward Jeffrey Wright, but not the righteousness of the Southern cause. This is what makes McGuire's character unique - and his loyalty suspect to some of his fellow guerrillas.
Among other standout performances are Jonathan Rhys-Meyers and Jewel. Rhys-Meyers character is like watching a slowly uncoiling viper, perhaps not menacing at first, but as the film progresses you begin to realize he is a stone-cold killer, untroubled by remorse or conscience. Jewel is also impressive - this is the only film I have ever seen her in. I am not into her music so I never paid much attention to her, but her work here is memorable and perfect for the role she plays.
The climax of the film is the infamous raid on Lawrence, Kansas, when the various Rebel guerrilla bands came together to launch a strike deep into Union territory. The depiction of the raid is quite moving and haunts the viewer afterward. It is also historically accurate from what I have read, including the detail that the Confederates saw it as justified vengeance for what they perceived (mistakenly as it turned out) as an earlier atrocity. Regardless of their motives, the attack was one of the worst atrocities committed on American soil. The movie pulls no punches in showing the ominous buildup to the raid and what happens when the hordes of mounted guerrillas descend on the unsuspecting town.
Ang Lee deserves a lot of praise for Ride with the Devil. For a Hong Kong director to make such a startling and realistic period piece about one of the most savage and little known theaters of conflict in the American Civil War is remarkable in my book and I salute him for the achievement.
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