14. Heaven's Gate (1980)
Actual film aside, Michael Cimino's infamous box-office disaster Heaven's Gate would be considered a "dark" Western based solely on its reputation—fair or not—for ending the golden age of '70s Hollywood auteurism. Ironically, one of the themes of Heaven's Gate is the danger of hubris, as rich land barons plot to kill poor immigrants and take their land. Coming off The Deer Hunter, Cimino once again examines the damage wrought by an imperialist force in an uncivilized land on both the enemy combatants and its own soldiers, represented once again by gun-for-hire Christopher Walken. But the meandering story is ultimately left in the dust—pun intended—by Vilmos Zsigmond's breathtaking cinematography, described by detractor Roger Ebert as "so brownish yellow that you want to try Windex on the screen."
15. Unforgiven (1992)
Like the David Bowie of Westerns, Clint Eastwood reinvented his chosen genre across decades while remaining faithful to its core. The iconic cowboy could play white hats, black hats, gray hats, and—in the case of 1992's Unforgiven—a hat so morally muddy, it's almost no color at all. Eastwood plays a put-to-pasture desperado who gets back in the game for one more hit, only to find that age, alcohol, ambivalence, and the collapsed myth of the West are all stacked against him. Grating against Gene Hackman's crusty sheriff, Eastwood plays every grit-scoured wrinkle to the hilt—and the film's fistfights are as brutal as its gunplay. (At least, if someone getting blasted in the face with a rifle at point-blank range can be considered "gunplay.") Reclaiming the dusty oater from Young Guns, which immediately preceded it, Unforgiven was a hit, and Eastwood won the Best Picture and Best Director Oscars the year of its release. Tellingly, it was also the last Western Eastwood has made—and its allusions to everything from Shane to Eastwood's own towering The Outlaw Josey Wales make Unforgiven even more morbidly poignant.
16. Dead Man (1995)
Jim Jarmusch's surreal, bleak, wry arthouse take on the Western stars Johnny Depp as William Blake, a hapless Eastern accountant forced to go on the run after he kills another man in self-defense. He falls in with a philosophical, sweetly naïve Indian man named Nobody (Gary Farmer, in a film-stealing performance), who mistakes Depp for the long-dead English poet William Blake, and guides him on a journey to the Pacific coast that's also a metaphorical journey into the afterworld. The two encounter a series of characters representing the uglier side of civilization (evil, belligerent mine tycoon Robert Mitchum, in his last role) and the frontier (a trio of rustic goons, including a cross-dressing Iggy Pop). But the biggest surprise for Blake is his own fate, as it turns out he may not have survived that gunfight back at the beginning of the movie after all…
17. The Proposition (2005)
Given Nick Cave's love of murder ballads, it's no real wonder that he'd script a film this unrelentingly grim, but it can still be hard to stomach the way the storyline wallows in blood and grime. Guy Pearce plays an Australian outlaw who runs afoul of lawman Ray Winstone after a messy shootout, apparently one of many. Winstone proffers a deal: If Pearce tracks down and kills his older brother, unrepentant worst-of-the-lot criminal Danny Huston, Winstone will release Pearce's younger brother (Richard Wilson) instead of hanging him on Christmas Day. While Pearce mucks about in the desert, confronting Huston and apparently considering his conflicting obligations to his kin. From there, the story just heads deeper and deeper into misery, with torture, attempted rape, stunningly vicious beatings, and mass murder all looming into the picture. It felt grim in the '50s when a lawman won a fight but lost his hope. Here, everyone starts with no hope and goes on to lose their souls and their lives, usually in that order.
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