Classic Westerns: Our All-Time Best Movie Cowboys

by Suzanne Halliburton

In classic westerns, the cowboy always is a complex character. There are layers to him. He can be the soulful good guy, the anti-hero fighting for revenge or maybe the rancher leading a bunch of kids on a cattle drive.

We here at Outsider decided to come up with a list of our favorite movie cowboys in Hollywood’s classic westerns. There are no wrong answers or rankings.

Here’s how we see it. Enjoy our classic western heroes:

Roy Rogers Gave Us Classic Westerns In Radio, TV Film

OK, Rogers, ranked No. 7, defines cowboy in classic westerns. Back in the day, folks called him the “King of the Cowboys.” We knew his wife — Dale Evans. We knew his horse — a Golden Palomino named Trigger. And we even knew his dog — Bullet, the German Shepherd. He so dominated the cowboy market that Roy Rogers’ show was on radio and then on television.

His given name was Leonard Franklin Slye and he was born in Cincinnati. Friends called him Len. He gained his stage name of Roy Rogers in 1938 after he’d been in a movie with Gene Autry, the original singing Cowboy. In the majority of his movies, Roy Rogers played a Cowboy named Roy Rogers. A classic name for classic westerns.

Rogers also was a smart businessman. After all, in 1940, he asked his lawyers to negotiate a contract clause giving him the rights to his name, likeness and voice. Because of this, little boys could play with Roy Rogers action-figures. He even had a line of restaurants named for him.

Rogers sported his own theme song — “Happy Trails.” And keeping it in the family, Dale Evans wrote it. Rogers filmed his last western in 1975 outside Lubbock, Texas. He died in 1999

Henry Fonda Played The Everyman And The Bad Guy

Fonda, No. 6 on our list, was one of the world’s best actors. But most fans knew him as the walking-talking embodiment of the Cowboy Code. He portrayed Wyatt Earp in “My Darling Clementine.” And he starred in two classics, “How the West Was Won” and “Once Upon a Time In The West.”

Fonda played so many good guy roles in classic westerns he claimed to a reporter “I’m not really Henry Fonda, nobody could have that much integrity.”

He did play sympathetic outlaws in his first two classic westerns, “Jesse James: and “The Return of Jesse James.” Maybe he wanted to go against type in his final important western. Fonda played a killer in “Once Upon a Time In The West.”

Even Fonda’s two children, Henry Fonda and Jane Fonda, acted in westerns. Henry Fonda died in 1982. The American Film Institute selected Fonda as the sixth greatest star of all time.

Yes, James Stewart Was a Cowboy

James ‘Jimmy’ Stewart might be known for other roles. Maybe you think of Stewart, who is No. 5 on out list of top cowboys, as the idealistic Mr. Smith in “Mr Smith Goes to Washington.” You know him as everyman George Bailey in “It’s a Wonderful Life.” But, Stewart had a huge role, playing opposite John Wayne in “The Man Who Shot Liberty Valance.”

Stewart played the anti-hero and helped popularize classic westerns to mass audiences. He made his Western debut in “Destry Rides Again.” He also starred in “How The West Was Won,” and “Winchester 73.”

It was in these movies that he developed the anti-hero style of cowboy and it was these characters who would dominate classic westerns for many years. Some of Stewart’s top movies include ‘The Man Who Shot Liberty Valance,” “Bend of the River,” “Destry Rides Again,’ ‘How the West Was Won’ and “Winchester 73.” Plus, he played John Wayne’s doctor in “The Shootist.” So yes, you may think of Jimmy Stewart as George Bailey, but he’ll always be a classic cowboy.

Stewart died in 1997.

Will Rogers Never Met a Cowboy He Didn’t Like

Rogers, the folk and political humorist, made this line famous — “I never met a man I didn’t like.” But trust us, Rogers, in his heart, was a classic cowboy. He’s No. 4 on our list and made it because he was a real-life cowboy who sometimes played one in films. Three of the best films were classic westerns — ‘Old Kentucky,” ‘State Fair,’ and ‘Judge Priest.’

Before he got his big break, Rogers made ends meet as a cowhand in Oklahoma. His first act as an entertainer was as a roper in a vaudeville show. For a decade, he worked with a pony and a rope, enchanting crowds at a roof-top theater. He was deemed “America’s Favorite Cowboy.” But we’re sure that Gene Autry and Roy Rogers would want a word.

Rogers and aviator Wiley Post died in 1935 when their small plane crashed in northern Alaska. His obituary included many accomplishments, Oklahoma cowboy helped launch them all.

Gary Cooper Won an Academy Award As a Cowboy

Cooper, who we rank as the third-best cowboy, was a terrific actor. He won two Academy Awards. He’ll always be Marshal Will Kane in “High Noon,” one of Hollywood’s best among the classic westerns. He also had roles in ‘The Plainsman,’ “Vera Cruz,” “Man of the West,’ and “The Westerner.”

Coincidentally, Cooper played a cowboy in the first-ever Western with sound. That was “The Virginian” in 1929. Cooper played a ranch foreman in Wyoming. He romanced the local school teacher and his best friend was a cattle rustler.

Cooper died in 1961.

Clint Eastwood Played Cowboys Looking For Revenge

Eastwood, at 90, is the only actor/cowboy on our list who still is alive. We rank him at No. 2.

Eastwood accomplished it all in classic westerns, from acting, producing and directing. He also played the gamut of characters. He’s always was the conflicted soul. Revenge often was a theme. Some of his characters had no names.

Eastwood’s cowboy dialogue was terrific, too. Remember “you know, you’re going to look awfully silly with that knife sticking up your ass,” from “High Plains Drifter.”

Or from “A Fistful of Dollars: “I don’t think it’s nice, you laughing. You see, my mule don’t like people laughing. He gets the crazy idea you’re laughing at him. Now if you apologize, like I know you’re going to, I might convince him that you really didn’t mean it.”

Eastwood won two Academy Awards for Best Director and Best Picture with Unforgiven in 1992. That’s probably the best among modern-day westerns. He starred in several classic westerns, including  “The Good, The Bad and The Ugly,” “The Outlaw Josey Wales,” Hang ‘Em High” and “Pale Rider.” Seems appropriate that his role in the TV series “Rawhide” launched his movie career.

John Wayne Consensus All-Time Cowboy

There’s no arguing with this — Wayne is the best-known cowboy of them all. John Wayne defined classic westerns. His characters were unforgettable. He was Ringo Kid in Stagecoach, his breakout role. Or Rooster Cogburn in “True Grit.” Or cattle rancher Wil Anderson in “The Cowboys.” Or Sheriff John T. Chance in Rio Bravo. Or Tom Doniphon in “The Man Who Shot Liberty Valance.”

Wayne’s final movie was “The Shootist.” He brought J.B. Books, the aging gunslinger, to life.

Wayne defined the cowboy as a classic movie character. He had his own distinct walk and bark of a voice. “The Duke” was the quintessential complex cowboy, playing the good guy to the anti-hero.

He died in 1979.