10 Best Outlaw Western Movies, Ranked

Movies


A good many Westerns (particularly the older ones made closer to the middle of the 20th century) revolve around tales of good versus evil. For sure, when such a film is done well, it can be undeniably satisfying to see a heroic sheriff or gunman stand up to bandits or corrupt individuals and defeat them, often fighting violence with violence. But it’s unlikely such things would’ve actually occurred in Old West times, and as such, some movies specialize in taking a less black vs. white approach narratively.


Some of these films can be classified as outlaw Westerns which, as the name suggests, tend to revolve around those on the other side of the law, perhaps even making lawmen on the “right side” of the law the antagonists. It can be more thematically complex to have morally gray characters in such stories, and there’s an argument to be made that such Westerns are also a little more fun and less predictable. Some of the best outlaw and/or antihero Westerns are ranked below, starting with the good and ending with the great.


10 ‘The Good, The Bad, The Weird’ (2008)

Director: Kim Jee-woon

Image via CJ Entertainment

Not to be mixed up with a certain 1960s Western with a similar title (more on that one below), The Good, The Bad, The Weird is a Korean film that’s as ridiculous and entertaining as it is action-packed. It has a story set in Manchuria during the 1930s, nevertheless retaining the feel of a classic Western (and perhaps gently spoofing the genre; almost) as it follows three outlaws who are all seeking treasure hidden somewhere in the desert.

The Good, The Bad, The Weird races forward at a speed that makes plenty of other fast-paced movies look slow in comparison, and it’s a blast to watch from start to finish. All the characters are flawed – some more than others – but they’re all interesting and have plenty of good dynamics between each other. Even if they didn’t, the action here alone, which is frequent and of a very high quality, is worth the price of admission.

The Good, The Bad, The Weird

Release Date
July 17, 2008

Director
Jee-woon Kim

Cast
Song Kang-ho , Lee Byung-hun , Jung Woo-sung , Oh Dal-su

Runtime
130 minutes

Watch on Tubi

9 ‘The Proposition’ (2005)

Director: John Hillcoat

The_Proposition_Nick_Cave
Image via First Look International

Not only does The Proposition contain numerous cutthroat and morally complex characters, but it would also have to rank up there as one of the most brutal and bloody Westerns of all time. Its plot concerns a man who’s forced to make an impossible decision, as he’s told his younger brother will be killed if he doesn’t successfully hunt down and kill his older brother, who’s an outlaw at large.

The world of The Proposition is a nasty and hopeless one, but the film is nevertheless compelling, thanks to its intriguing premise and the complex moral questions it demands of its characters and audience. As far as Westerns revolving around outlaws go, it’s certainly one of the heavier ones, but those who don’t mind a Western that can be a bit emotionally demanding and grim ought to give it a shot.

The Proposition

Release Date
October 6, 2005

Runtime
104

Main Genre
Crime

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8 ‘The Outlaw Josey Wales’ (1976)

Director: Clint Eastwood

Clint Eastwood shooting with a gun in each hand in The Outlaw Josey Wales
Image via Warner Bros

Clint Eastwood rose to prominence as an actor within the first decade or so of his career in the world of film, but by the early 1970s, he was also finding success as a director. Every so often, he would direct a film and star in it, in some capacity, with The Outlaw Josey Wales being one of the first times he did this to great success. To this day, it remains one of the best Westerns Eastwood’s ever been associated with.

It’s no surprise that it can count itself as an outlaw Western, given its title, and the story itself revolves around the legendary titular character; a feared avenger who gets bloody revenge for wrongs committed against himself, and then protects the downtrodden in the Old West by any means necessary. Though the main character is violent and ruthless, The Outlaw Josey Wales shows the West to be a dog-eat-dog kind of place, making the protagonist ultimately feel like something of an antihero.

The Outlaw Josey Wales

Release Date
June 30, 1976

Cast
Clint Eastwood , Chief Dan George , Sondra Locke , Bill McKinney , John Vernon , Paula Trueman

Runtime
135 minutes

Main Genre
Western

Rent on Apple TV

7 ‘The Assassination of Jesse James by the Coward Robert Ford’ (2007)

Director: Andrew Dominik

Casey Affleck pointing a gun at someone in 'The Assassination of Jesse James by the Coward Robert Ford' (2007)
Image via Warner Bros. Pictures

One of the great Westerns of the 21st century (therefore being one keeping the genre alive, even past its arguable heyday), The Assassination of Jesse James by the Coward Robert Ford has a plot that’s mostly summarized by its title. It does indeed revolve around that infamous event, showing the complex feelings Ford had towards James, exploring why he did what he did, and then showcasing how it impacted the rest of his life.

Those who like their Westerns packed with action and heroics might not find a lot to love with The Assassination of Jesse James by the Coward Robert Ford, because it’s dark, patiently paced, and character-focused. Yet it’s one of the most morally complex and thought-provoking Westerns, not just of its kind, but of any within the genre broadly speaking, and is likely a film that will go on aging incredibly well.

Rent on Apple TV

6 ‘Pat Garrett & Billy the Kid’ (1973)

Director: Sam Peckinpah

Pat Garrett And Billy The Kid - 1973
Image via Metro-Goldwyn-Mayer

Sam Peckinpah was no stranger to Westerns featuring rough-around-the-edges characters who tended to get involved in exceedingly violent conflicts. Of his various films, Pat Garrett & Billy the Kid is both one of his best and one of his most overlooked, not getting the kind of love it deserves despite telling an excellent and dramatic story about friends turned rivals, and the heartbreak/anger that comes with such a turn of events.

That’s not to say Pat Garrett & Billy the Kid lacks entertainment value or is otherwise devoid of excitement/action, but it is a downbeat affair overall, and all the better for it. Not only are various characters outlaws, but they’re all downtrodden and struggling to get by in their own ways, which is depressing, yes, but also feels perhaps more true to life than other Westerns out there with sunnier dispositions and more clear-cut heroes and villains.

Rent on Apple TV

5 ‘The Hateful Eight’ (2015)

Director: Quentin Tarantino

Samuel L. Jackson as Major Marquis Warren in The Hateful Eight
Image via The Weinstein Company

The Hateful Eight is one of the most violent films Quentin Tarantino has ever made, and might also be up there as his most intense and horrific. The main characters are all various shades of hateful and aggressive, as the title implies, and so when they all find themselves in a confined location while waiting for a raging blizzard outside to stop, tensions build and violence seems like an inevitability.

Even though it’s hard to call any character within The Hateful Eight likable, some are more unlikable than others, meaning there’s still at least a little by way of emotional engagement throughout, particularly as the movie reaches its climax. It’s one of the most cynical and grimly violent Westerns ever made, relishing the fact that none of its characters are good people, and they generally become less kind when forced into the situation they ultimately find themselves in.

The Hateful Eight

Release Date
December 25, 2015

Runtime
182

Main Genre
Western

Watch on Netflix

4 ‘Hell or High Water’ (2016)

Director: David Mackenzie

Chris Pine in 2016's Hell or High Water
Image via Lionsgate

Perhaps feeling more like a crime movie than a Western, however you want to classify Hell or High Water, it is, at the end of the day, a great film. While it doesn’t take place during Old West times, it nevertheless maintains the spirit of the Western genre, and follows two brothers who are in a desperate situation and need money, forcing them to carry out various ambitious bank robberies.

The main characters are sympathetic “outlaws,” in a sense, while the film also features two lawmen who are in pursuit of these brothers, both of them also likable in their own way. Tragically, these two duos are destined to crash, leading to an immense amount of tension and emotion throughout. Hell or High Water’s good enough that even those who don’t usually like Westerns should have a blast here, and those who do like Westerns will find it inevitably ticks all the boxes it needs to.

Hell or High Water

Release Date
August 12, 2016

Director
David Mackenzie

Runtime
102

Main Genre
Crime

Rent on Apple TV

3 ‘Butch Cassidy and the Sundance Kid’ (1969)

Director: George Roy Hill

Paul Newman as Cassidy and Robert Redford as Sundance on horseback turning to face the camera in Butch Cassidy and the Sundance Kid
Image via 20th Century Studios

One of those rare movies that feels like it’s close to perfect, Butch Cassidy and the Sundance Kid is also the kind of classic film that hardly needs an introduction. Its titular characters are Old West outlaws of the most lovable variety (the fact they’re played by Robert Redford and Paul Newman helps), with much of the plot revolving around the lengths they go to while escaping the law after perhaps one robbery too many.

Butch Cassidy and the Sundance Kid is quite possibly the best buddy movie that’s also a Western, with great chemistry between its two leads, plenty of humor and heart, and some well-shot and exciting action peppered throughout. It’s great entertainment and also feels easy to go back and revisit time and again, making it undeniably one of the all-time great outlaw Western movies.

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2 ‘The Wild Bunch’ (1969)

Director: Sam Peckinpah

William Holden, Ernest Borgnine, Ben Johnson, and Warren Oats in The Wild Bunch
Image via Warner Bros.

Some years before Pat Garrett & Billy the Kid, Sam Peckinpah made what’s often considered his greatest film with The Wild Bunch. The main characters here make up a gang of outlaws who are generally starting to feel like their best years are behind them, and they may need to pull off one final score and call it quits. Other people and/or fate itself have other plans, though, and complications ensue… as does a great deal of bloodshed.

At the time it was released, The Wild Bunch was considered shockingly violent, and though it’s been exceeded in that department by other films since, it still has the capacity to shock and awe viewers to some extent. It’s up there with the greatest movies made in the 1960s, and films about bands of outlaws trying to get by during unforgiving and brutal times don’t get much better than this.

The Wild Bunch

Release Date
June 19, 1969

Director
Sam Peckinpah

Main Genre
Western

Rent on Apple TV

1 ‘The Good, the Bad and the Ugly’ (1966)

Director: Sergio Leone

The Good, The Bad, and The Ugly - 1966
Image via United Artists

Like 2008’s The Good, The Bad, The Weird, 1966’s The Good, the Bad and the Ugly follows three immoral characters all doing what they can to uncover some sort of treasure buried in the desert. The titular Good isn’t exactly a good guy, but he’s not as ruthless as the Bad. The Ugly is somewhere in between, perhaps being the most endearing and memorable character because he’s a wild card and something of an underdog compared to the other two.

They clash and form uneasy alliances throughout, all before the film concludes with one of the best finales in cinema history. The Good, the Bad, and the Ugly is one of those classics that was somehow ignored by the Oscars, yet it lives on to this day as, some would argue, the greatest Western of all time. As such, it’s pretty easy to select it as the best Western revolving around outlaws and shady (yet compelling) characters.

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