Since its inception, the Western film genre has revolved around the never-ending conflict between the dogged upholders of law and order and the rebellious scofflaws who have given in to the temptations of the Wild West. In the early days of the genre, this conflict was portrayed as a simple and classic struggle of good vs. evil, but soon stories evolved and began to show many of the dastardly bandits in a more sympathetic light.
Looking back at the ever-growing canon of Western films today, movie lovers will see a vast array of protagonists that belong to either the lawman or the outlaw class, sometimes even blurring the line between the two. In the list below, we’re taking a look specifically at the best outlaw heroes – or anti-heroes – of the Western genre!
William Munny – Unforgiven (1992)
Unforgiven is a classic ‘90s Western about an aging outlaw who’s brought back into the saddle to hunt down a band of cowboys who slashed up a young prostitute.
The lead ex-outlaw is William Munny, played by the always-amazing Clint Eastwood. and he’s a great anti-hero to root for. Sure, he’s lied, cheated, and stolen in his past. He’s even killed before, but his determination to leave the violent lifestyle behind is admirable. In fact, the entire movie centers around the conflict in his heart about abiding by the law and doing what he thinks is right, making him a highly nuanced character that the audience wants to see find his peace.
Frank Talby – Day of Anger (1967)
While both of the main characters are intricately detailed and brilliantly portrayed, it is the tough-as-nails Talby that we love to root for. He’s played by the great Lee Van Cleef, and has an intense smolder and an ultra-badass aura about him, as well as a remarkable amount of pathos that makes him easy to sympathize with.
Trinity – They Call Me Trinity (1970)
They Call Me Trinity is a spaghetti western comedy that balances all the violent, stylized shootouts the Italian Western is known for with a welcome dose of wacky hijinks and slapstick.
The film chronicles the exploits of the titular outlaw, Trinity, whose lazy but quick-witted antics keep him alive on the dangerous frontier, and have garnered him a reputation known far and wide. Though he scoffs in the face of law and order, Trinity is willing to stand up to evildoers and put his life on the line for a good cause, which he does when he helps a peaceful community fend off a gang of vicious bandits.
Billy the Kid – Pat Garrett and Billy the Kid (1973)
Pat Garrett and Billy the Kid is an underrated Western about the storied friendship and subsequent rivalry between the titular sheriff and outlaw. Directed by Sam Peckinpah, the go-to guy in the late ‘60s and early ‘70s for ultra-violent and philosophical revisionist westerns, the movie notably humanizes and deconstructs the near-mythic character of Billy the Kid.
Billy the Kid is at once a thoughtful friend and a heartless backstabber, which makes him a complex character. Brought to life brilliantly by country music legend Kris Kristofferson, Billy the Kid is an easy outlaw to root for, because the goodness within him is apparent, and one wants to see him find solace for his inner turmoil.
Rio – One-Eyed Jacks (1961)
One-Eyed Jacks is a pivotal Marlon Brando classic in which the legendary actor portrays an outlaw by the name of Rio, who is double-crossed by his greedy partner after pulling off a major bank heist. Rio lands in jail and cools off there for years, all the while plotting his vengeance.
Rio is a fascinating character because he has both an incredible determination for having his revenge and a lonely heart that yearns for love. Brando portrays this contradictory character perfectly, and makes the outlaw one of the most iconic western film protagonists of all time.
The Wild Bunch – The Wild Bunch (1969)
Another one by the macho and rebellious Sam Peckinpah, The Wild Bunch tracks the efforts of an aging outlaw gang dead-set on pulling off one last heist before they throw in the towel for good. The Wild Bunch, according to Roger Ebert, “presents death and violence in such definitive (indeed, even excessive) terms that it becomes, paradoxically, a statement against violence and a reaction to it.” Indeed, the film is thematically centered around the inevitability of death and violence, and our aging anti-heroes perfectly personify these heady concepts.
Since the movie follows a team of outlaws, each uniquely characterized and perfectly portrayed by their respective actors, we’re including the whole posse on this list. Led by William Holden’s Pike Bishop, the gang consists of Dutch Engstrom, played by Ernest Borgnine, and the brothers Tector and Lyle Gorch, played by Ben Johnson and Warren Oates, respectively. They’re an easy group to root for, because, despite their gruffness and tendency towards violence, they have an easy-going camaraderie and an underlying sadness that makes them very sympathetic.
John McCabe – McCabe & Mrs. Miller (1971)
One of celebrated director Robert Altman’s most powerful films, McCabe & Mrs. Miller is a powerful revisionist western drama from acclaimed director Robert Altman. It follows an outlaw gambler who moves to a dreary little mountain town and, along with his prostitute partner, sets up a successful business. Soon, a major corporation tries to steal their business out from under them.
The outlaw we root for in this picture is the McCabe of the title: John McCabe, a quick-witted gambler who’s rumored to be the fastest gun around. Although he easily outsmarts many people throughout the movie, one gets the sense that McCabe is something of a born loser; unrequited love and an ever-loosening grip on the enterprise that gives him purpose morph the rugged outlaw into a pitiable character that just can’t seem to get his mojo back.
Josey Wales – The Outlaw Josey Wales (1976)
The Outlaw Josey Wales is a Clint Eastwood-starring classic Western that follows the titular outlaw on a quest for revenge on the soldiers who murdered his wife and child.
Josey Wales is a nuanced character that is both bloodthirsty and tragically broken-hearted, and Eastwood does a wonderful job bringing him to life. As the film progresses, Wales’ bloodlust lessens as he begins to fall in with a sort of surrogate family that fills the void in his soul. Unfortunately, his newfound peace doesn’t last long, as a big bounty on his head brings trouble back into his life.
Jesse James – The Assassination of Jesse James by the Coward Robert Ford (2007)
The Assassination of Jesse James by the Coward Robert Ford is a stunning modern classic of a Western about the infamous outlaw Jesse James and his attempts to evade the multitudes of bounty hunters bent on claiming the high price on his head.
In the words of Collider, “Dominik’s filmmaking and Brad Pitt’s performance as this outlaw, among many other qualities, peel back the legendary layers to reveal the deeply vulnerable human given that inescapable name, Jesse James.” Indeed, Pitt as the titular Jesse James is an amazing performance to behold, giving grace, poise, and intricately-detailed characterization to the mythical outlaw.
The Man with No Name – Dollars Trilogy (1964 – 1966)
A Fistful of Dollars, For a Few Dollars More, and The Good, the Bad, and the Ugly – collectively known as the “Dollars Trilogy” – are some of Clint Eastwood’s best-ever movies and three of the finest spaghetti westerns ever made. The three films are mostly unrelated plot-wise, but are connected by sharing Sergio Leone’s masterful direction, many of the same themes, and, of course, Eastwood as the legendary “Man with No Name.”
In all three highly influential masterpieces, Eastwood plays a mysterious outlaw who tricks and outwits those around him for personal gain. Despite his greedy goals, however, the character is incredibly easy to root for. Not only is he one of the coolest dudes in cinema history, but the occasional glimpse beneath the surface reveals an inner kindness – such as the famous moment in The Good, the Bad, and the Ugly in which he comforts a dying young soldier on a Civil War battlefield.
Butch Cassidy and the Sundance Kid – Butch Cassidy and the Sundance Kid (1969)
Butch Cassidy and the Sundance Kid is a Western masterpiece about a duo of likable outlaws who attempt to ride down to South America in order to escape hefty prices on their heads.
Screen icons Paul Newman and Robert Redford star as the titular outlaws, and command the audience’s attention and reverence with their fun-loving nature and tenacious commitment to finding freedom in a changing “New Western” frontier. In the end, the pair wind up being the ultimate martyrs for freedom, which makes them the ideal candidates for outlaws we love to root for.