As long as the focus is on Mia and Elliot, the film is involving and moving.
Ang Lee is by now no stranger to audience indifference. His subject matter is all humane sensitivity and gentle issue exploration, how could he not leave some people unmoved just on general principal in this country. Riding high from the combined successes of his marvelous adaptations of “Sense & Sensibility” and “The Ice Storm,” branching into oater territory to plead for racial equality in the 90s couldn't possibly have seemed like that big a gamble? After all, he cast just about every handsome young face Hollywood had to offer, and for anyone looking for connections to historical westerns, there were plenty, right down the Nicholas Ray inspired colourful smocks his young heroes sport throughout. It seemed failure proof. And yet it only made back about 20% of its budget and critics knew it was impressive but few really want to bat for it at the time. Ebert himself didn't think it was entertaining.
I think he may be onto something, as far as it goes. “Ride with the Devil” isn't really out to entertain. It's a film about the incredibly harsh truths of young men with guns. The 90s had already seen a lot of incredibly tense violent stand offs and no one would have any way of knowing that the problem would get so much more worse and much more visible in the decade and change since. Lee is not a combat director, he's a chaos director (but he still does it with a painter's eye - his scenes of battle here have the grand scale and colour modulation and tonality of great early American art), because chaos is what he takes away from battle. Not valour, not glory, just insanity. And "Ride with the Devil" is about that very insanity. You see it creep into the eyes of characters played by Jonathan Rhys-Myers and Simon Baker, the way killing for so long with such impunity, such steadfast conviction, will turn you away from yourself, and out from your eyes pours a stare of deep loss of life and loss of the self. They may as well be empty sockets. It's seen as a major victory when these men can finally settle their problems without bloodshed. Finally reborn under what our own Godfrey Cheshire calls "the elusive goddess of freedom," in his essay for the film's Criterion release.
This film did find its audience, slowly, but remains a film most people have to look up when you mention its name. Someday when Lee's canon is being parsed and summed up, after all his many twists and turns, this film will emerge as one of his finest works.
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