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Cowboy Up: Five Favorite Westerns

Most of my life (maybe even now) I’ve dreamed of being a cowboy. What kid hasn’t, especially here in Colorado where America’s most enduring icon remains remarkably relevant in the form of working ranches and mini Steamboat or Antonito cattle drives? And as much as I was inspired by the open plains, endless peaks and thoughts of riding the high country, I fed that inspiration with Gunsmoke and Bonanza reruns, Louis L’Amour novels and about 20 to 50 viewings of most every Western ever made.

John Wayne was and is the king of the Western, especially in movies such as The Searchers, Fort Apache, The Cowboys and Rio Bravo. But for my generation it was Butch Cassidy and the Sundance Kid and every Clint Eastwood spaghetti shoot-em up from a Fistful of Dollars to Hang ‘Em High to, especially, The Good, The Bad and Ugly that provided a more modern, more menacing sense of cold-blooded frontier cool. For folks looking for a little more box office bravado, there might be a preference for the Technicolor take of Tombstone (with Val Kilmer playing it to the hilt as Doc Holliday), the perfectly pitched little cattle war of Open Range, or the cliché loving camp of Silverado, which for me, has unfortunately aged the worst of them all.

Which is not to say that I wouldn’t tune in if it was on TNT or AMC this Friday when I came home from the bar. Anyway, here are my five favorite Westerns. My only rules were not to duplicate any lead actors, and really to focus on what resonates with me the most. I’d certainly like to hear about your picks, and why they mean what they mean to you.

High Noon

(1952, Gary Cooper, Gracy Kelly, Ian MacDonald)

High Noon established the Western as the ultimate morality play, where you knew several someones were going to get shot, and the only question was who would still be holding a gun when the curtain fell. Cooper as Will Kane, the marshal, is left alone by everyone in town, including his gorgeous Quaker, non-violence preaching wife Amy Fowler (Kelly) to face the outlaw gang of Frank Miller (MacDonald), who is returning on a train at the aforementioned time in the title. Anyone who ever saw this flick figured they’d be the one person in town to stand with Will, but it’s Amy who shoots one of the outlaws dead to save her husband, and Kane who gives the town the finger, flipping his badge into the dirt after the shootout to end the story.

True Grit

(1969, John Wayne, Kim Darby, Glen Campbell)

When U.S Marshal Rooster Cogburn (Wayne) faces Lucky Ned Pepper (Robert Duvall) and his gang in an open field, proclaiming that he intends to kill Pepper or see him hang, Pepper replies, “That’s mighty bold talk for a one-eyed fat man.” Wayne’s incensed answer, “Fill your hand you sonofabitch,” may be the greatest line in Western history. Shooting them all down with the reins to his horse like a bit between his teeth—while ‘Texican’ La Bouef (Campbell) finishes off Pepper with a rifle shot from a ridge—only seals the victory. Special points are earned for the Colorado-based cinematography, and the fact that Wayne won an Oscar for the role. But it’s Mattie’s (Darby) role as an utterly no-nonsense girl seeking revenge for her father’s death that really carries this movie.

The Wild Bunch

(1969, William Holden, Ernest Borgnine, Robert Ryan)

Full disclosure: this is my favorite movie. The fact it was made the same year as True Grit, a kind of PG-13 Disney tale at heart, still blows my mind. That’s because when it comes to violent realism, The Wild Bunch is The Fully Monty. Holding together an aging, feuding gang of outdated outlaws across a final series of raids from Texas to Mexico, Pike Bishop (Holden), and his lieutenant Dutch Engstrom (Borgnine) are as ready to kill as they are to philosophize their reasons for killing. Betrayed gang member Deke Thornton’s (Ryan) chase of them, only adds to the sense of indifference between justice and final gory glory. All of which leads to a final outrageous shoot-out unmatched by anything other than Spielberg’s treatment of D-Day. Throughout, the term, “Let’s Go,” has never been so weighty.

The Outlaw Josey Wales

(1976, Clint Eastwood, John Vernon)

This is my only Clint pick, so let’s clear the air. All the Sergio Leone directed movies are bona fide classics, and I re-watch them all regularly. But long before High Plains Drifter’s six-gun mysticism slipped into Pale Rider (where the final shootout really does suck), I kind of lost the thread of the all-knowing borderline ethereal killer. And even the brilliance of Unforgiven is still just a reworking of Wales, where the embittered gunman-turned-farmhand can’t resist his violent skills, especially in the face of obvious pistol-packing lessers. I personally count eight classic shootouts from minor to major over the course of this film, an ongoing how-to regarding professional gunfighting, and the timeless line, “Dyin’ ain’t much of a livin’” from Wales to an eternity-bound bounty hunter.

No Country for Old Men

(2007, Tommy Lee Jones, Javier Bardem, Josh Brolin)

There were certainly a few wild cards considered here, from Dead Man to Blazing Saddles to One Eyed Jacks. But No Country for Old Men I believe is the eerily accurate template for where the Western will continue to go in the future. Not just because the massacre and money that Llewelyn Moss (Brolin) finds are connected to drugs, setting the murderous spree of Anton Chigurh (Bardem) in motion. Or because Chigurh is a super creepy hitman with a seemingly compulsive joy for his work beyond the realm of any mere gunslinger. Or because Sheriff Ed Tom Bell (Jones) is a bit of an apocalypse preacher, seeing the end of days in the sins all around him. But more because this movie continues to remind us that in places like El Paso and Mexico, many people continue to live in the Wild West right now.

Please do add your own list of favorite Westerns in the comments section below

Peter Kray is EO’s editor-at-large and co-founder of the Gear Institute (

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