1. High Noon (1952)
Westerns are almost inherently grim: Traditionally, the quintessentially American genre would have us believe that the country was wrested from the wild by a few unrelentingly strong, stubborn, self-sufficient men bravely facing incredible odds and probable death. Still, Westerns tend to be about heroes, and heroes usually win. Which makes stark, morally muddy features like High Noon stand out. Gary Cooper won an Oscar for his portrayal of a weary-looking Old West marshal who, literally minutes after marrying Grace Kelly and hanging up his badge, learns that a killer he put in jail has been released and will be back in town for revenge in less than 90 minutes via the noon train. Operating in real time, Cooper re-dons his badge and scours the town, trying to assemble a posse to deal with the killer and his band, but all his friends and neighbors turn their backs on him, out of apathy, cowardice, denial, naïve hope that the problem will just go away, or even ambition for Cooper's job. As his hopes for help disappear one by one, Cooper looks increasingly strained and exhausted, and becomes more and more of a Christ figure, abandoned by his disciples and desperately wanting someone to tell him this cup will pass from him, yet holding to the courage of his convictions. In the end, Cooper dutifully faces the problem and triumphs, in a manner of speaking—he's alive, but his faith in humanity, virtually all his friends, and his belief in the things he spent his life fighting for are irrevocably gone. High Noon isn't about Western heroism, it's about surviving utter betrayal and moving on.
2. Track Of The Cat (1954)
Robert Mitchum plays a strong-willed son in a stressed-out ranching family; when a panther starts preying on their cattle, Mitchum takes to the hills, haunted by the words of an old Indian legend about animal spirits who exact revenge on greedy men. Meanwhile, back at the ranch, Mitchum's family plays out a psychodrama worthy of Eugene O'Neill, as their individual addictions—to liquor, to God, to love, to art—prove just as destructive as any wildcat. Veteran genre director William Wellman was at the peak of his Hollywood success when he made Track Of The Cat, and he was willing to take chances, turning an offbeat psychological Western (based on a novel by Walter Van Tilburg Clark, adapted by screenwriter A.I. Bezzerides) into a tone poem about man's uneasy relationship with nature.
3. Run For Cover (1955)
When James Cagney and his young riding partner John Derek take potshots at some birds flying above a passing train, the panicky railroad guards throw out sacks of money, assuming they're being robbed. Cagney and Derek try to return the money, but Derek gets shot and crippled by a local sheriff. When the town realizes its mistake, Cagney is named the new sheriff, just in time to confront the tyranny of a marauding gang. Director Nicholas Ray, working from a script by Winston Miller (adapting a story by Harriet Frank Jr.) shuffles through some of his pet themes, including the poison spread by disaffected youth, and the inability of violent men to escape their past. Run For Cover builds to a final showdown in which lifetimes of mistakes and bad luck come to a fatal fruition.
4. The Searchers (1956)
The Searchers opens by introducing a happy family, then having most of them die horribly at the hands of Comanche raiders (or "the Comanch," as star John Wayne insists on calling them), but even that isn't the really grim part. The grim part is the rest of the film. As Wayne and the family's adopted son, Jeffrey Hunter, track the Comanche, many miserable years pass, and the question of whether Wayne's wee niece—the family's one survivor—will be found alive becomes a question of whether she'll be sane and fit for white-folk society even if they do. Once they finally do reach her, Wayne decides that living with (and, to his clear, vivid disgust, being sexually compromised by) Indians has tainted her, and he promptly tries to murder her. The only thing grimmer than the actual action is the inevitable question—at exactly what point along the way did Wayne decide that too much time had elapsed, and that his life had to be utterly devoted to wiping out his niece rather than rescuing her?
5. The Tall T (1957)
Director Budd Boetticher, screenwriter Burt Kennedy, and actor/producer Randolph Scott made a series of short, tough Westerns in the late '50s, usually featuring Scott as a loner-by-choice, tortured by a tragic past. The Tall T—based on an Elmore Leonard novel—has Scott playing a much brighter, more social loner who becomes embroiled in a kidnapping plot when the stagecoach he's riding on gets hijacked by dandyish villain Richard Boone and his henchmen. Boone's crew meant to rob a money-transporting stage, but they hit a passenger stage instead, and while they wait for their real quarry to arrive, they hold the passengers hostage, setting off a game of psychological give-and-take in which even the "good guys" reveal themselves as less than noble. That is, all except for Scott, who so impresses Boone with his integrity and leadership that in the movie's most poignant scene, Boone all but asks if he can join Scott at his ranch. The tragedy of The Tall T is that even when the wicked have a change of heart, they're still damned by the choices they made long ago.
6. Man Of The West (1958)
In the '50s, director Anthony Mann made a series of "psychological Westerns" starring prototypical good guy Jimmy Stewart, and dealing with the struggle to remain virtuous and ethical in a world where brutality and greed are increasingly tempting alternatives. Mann cast another famously upstanding leading man, Gary Cooper, in his disturbing final Western Man Of The West; Cooper plays a family man confronted by his murderous outlaw past when the vicious Lee J. Cobb robs his train. When Cooper and companion Julie London are taken captive, Mann explores the gray area between good and evil as Cooper is forced to revert to his "bad" self in order to do the "right" thing, suggesting that darkness and light in each person can't be separated.
7. No Name On The Bullet (1959)
During the psychological Western decade, more than a few movies dealt with the sad lot of the professional gunfighter, forever doomed to be challenged by young bucks who want to make their reputations by proving that they're faster on the draw. For example, the 1950 potboiler The Gunfighter followed a legendary assassin's disastrous attempt to sneak back to his old town to see his girl, while 1956's The Fastest Gun Alive considers a poor soul who tries to hide his talent for gunplay at each new town he enters, but continues to be goaded into proving his mettle. Perhaps the darkest of the '50s gunfighter movies is No Name On The Bullet, with Audie Murphy as a tricky killer who always gets his victims to draw first, so the law can't touch him. He descends upon one small town like a specter, promising to take one of the citizens out, but not saying who—which forces all the locals to point fingers at each other, speculating over which of them has earned Murphy's retribution. Murphy is the unbeatable force: the guilt that everyone hides, and the fear they can't disguise.
8. The Shooting (1967)
The Old West was a strange, fearful, and isolating place, according to Monte Hellman's strange, fearful, and isolating low-budget classic The Shooting. Often described as an "existential" Western, The Shooting has a conventional setup (an uneasy alliance of enemies must rely on each other to survive treacherous territory) that's presented as a most unconventional stream of dead ends, roads to nowhere, and futile attempts to see or understand what fate has in store. Millie Perkins hires bounty hunter Warren Oates to take her to the town where her son was killed. Already paranoid after his partner's murder and brother's disappearance, Oates discovers he's being tracked by Jack Nicholson, another bounty hunter and Perkins employee, itching to gun him down. An eccentric storytelling style coupled with the oppressive desert setting—so open, yet so claustrophobic—ensured that The Shooting wouldn't be widely seen until Nicholson became a name actor several years later.
9. Once Upon A Time In The West (1968)
When he made 1968's Once Upon A Time In The West, Sergio Leone had already won acclaim for helping usher in a new era of revisionist Westerns with the Man With No Name trilogy he made with Clint Eastwood. Leone was ready to abandon the genre, but he was enticed back in part by the chance to work with one of his favorite actors, Henry Fonda. The result is arguably his best film. Once Upon A Time takes as one of its major themes the destructive influence of the "civilizing" process, as a murderous turf war breaks out over the railroad line being built through the Arizona frontier. That motif, in which the supposedly good forces are the most evil, found its most shocking expression in the audacious casting of Fonda as the cruel, violent lead villain, though he was at the time iconic for playing virtuous heroes in movies like 12 Angry Men and The Grapes Of Wrath. As Leone told Fonda when convincing him to take the role: "Picture this: the camera shows a gunman from the waist down pulling his gun and shooting a running child. The camera pans up to the gunman's face and… it's Henry Fonda."
10. The Wild Bunch (1969)
Sam Peckinpah's lyrically violent story of the end of the Wild West leaves its audience almost nowhere to turn in its depiction of corruption, savagery, betrayal, and twisted machismo. William Holden leads a crew of aging professional robbers whose way of life is becoming impossible as the march of progress brings the force of law down on their necks. Holden's men are vicious thugs, but the other side consists of power-hungry dictators like Emilio Fernandez's Mexican general, and crooked lawmen vividly described by their reluctant leader as "egg-suckin', chicken-stealing gutter trash." The opening image sets the tone, as children watch a phalanx of ants overpower and kill a larger scorpion: In the end, they're all disgusting insects.
11. McCabe & Mrs. Miller (1971)
Director Robert Altman called his McCabe & Mrs. Miller an "anti-Western," and to be fair, it does skips a lot of the genre trappings; instead of cowboys, Indians, marshals, and desperadoes, it has grubby entrepreneur Warren Beatty, who comes out to the western frontier to launch a grubby whorehouse consisting of some grubby girls turning tricks in grubby tents. The whole thing is about as far from heroic as possible. Julie Christie classes the joint up when she becomes Beatty's partner and makes his "brothel" into a serious business concern, but she's no particular help when some mining-company reps decide to kill him for refusing to sell the business to him. Like Butch Cassidy And The Sundance Kid two years earlier, McCabe & Mrs. Miller has its wry, even lighthearted side, but the ending is shattering and brutal. The difference is that Butch and the Kid go out fighting, in a final flash of wild bravado; Beatty's McCabe, by contrast, tries to squirm out of his fate, only fights when he absolutely has to, and goes down ignominiously and alone, for a questionable cause, while the woman he loves obliviously indulges her drug habit above. It's like Altman was erecting a warning sign: "Look out, '70s cinema starkness starts here."
12. Pat Garrett And Billy The Kid (1973)
It's telling that Pat Garrett's name comes first in the title of Sam Peckinpah's profoundly sad, controversial final Western. By the time the original, studio-botched version of Pat Garrett And Billy The Kid was released in 1973, the Billy The Kid story was already pretty well-worn territory for Westerns, so the focus here is on the man hunting him. Once again, Peckinpah expresses ambivalence (if not downright hostility) toward the conformity of "decent" civilization in what amounts to a character study of once-proud, now-defeated lawman James Coburn, who is forced to destroy his surrogate son—and by extension, his older, purer self. In a sad twist of fate, Peckinpah's beautiful meditation on personal compromise wouldn't be seen as he intended until after his death in 1984.
13. High Plains Drifter (1973)
Revenge is a common theme in Westerns, but the cold fury of frontier justice doesn't get much colder than in Clint Eastwood's second directorial effort, a supernatural-tinged tale of vengeance based on a script by Shaft writer Ernest Tidyman. Eastwood plays a dark variation on the already dark Mysterious Stranger role he'd perfected in Sergio Leone's spaghetti Westerns, appearing out of the desert haze to protect an Arizona town threatened by three outlaws who have already killed the town marshal. But the townsfolk have gotten far more than they bargained for: Eastwood begins to make bizarre, sinister demands, including painting every building in town red and renaming the place "Hell." Soon, it's increasingly apparent that the targets of his righteous rage aren't just the outlaws, but the secret-keeping citizens as well. (The hardboiled tone sometimes goes too far, especially in the disturbing sequence in which the stranger responds to one woman's insults by raping her—and it's strongly implied that that's what she wanted.)
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.