Everyone loves to root for the outlaw in some of the best Westerns of all time, right? One of the great things about the genre is that usually the lines are clear, there are good guys and bad guys. White hats and black hats. Often, the guys wearing the black hats are not only the more interesting characters, but they are actually the ones fighting for good, or revenge, or whatever the supposed “good guy” is doing to harm. This is a list dedicated to those guys, the guys who are so bad they are good.
And don’t worry, I’ve included a handful of movies that are Western-adjacent that make sense for this list too.
Butch Cassidy And The Sundance Kid
While it’s not one of my favorite movies (despite loving Robert Redford and Paul Newman), there isn’t a better example of rooting for the outlaws than the classic Butch Cassidy And The Sundance Kid from 1969. It was an era where much of society was fighting the establishment, so it makes perfect sense that the outlaws would be the heroes at the time.
Young Guns
One of the most notorious, and weirdly beloved outlaws in the Old West was Billy the Kid (Emilio Estevez in Young Guns)and his gang, which included gunslingers like Doc Scurlock (played by Kiefer Sutherland), José Chávez y Chávez (Lou Diamond Phillips), Dick Brewer (Charlie Sheen), and more. It’s a defining Western of its era.
The Outlaw Josey Wales
You knew this one had to be on the list. In fact, there are a whole bunch of Clint Eastwood movies that belong here, but this one actually has “outlaw” in the name, so you know exactly what you’re getting into with The Outlaw Josey Wales, a classic Spaghetti Western.
Unforgiven
Decades after Clint Eastwood first made his name in Westerns, he directed and starred in maybe his best one ever with Unforgiven. With co-stars like Morgan Freeman and the late Gene Hackman, this Best Picture-winning film is a true masterpiece.
The Sting
The Sting isn’t technically a Western, but it sure feels like one in every way. Two “outlaws,” played by Robert Redford and Paul Newman, go up against a villain in a series of gambling events in this classic crime caper. It might have been set in a time just after the end of the “Old West,” but the vibe remains for sure.
Desperado
Robert Rodriguez‘s modern Western Desperado hit the indie film world with a giant explosion when it was released in 1995. It might be set in the ’90s, but it’s still a gunslinger looking for revenge for the murder of his lover. It doesn’t get more classic than that.
The Good, the Bad and the Ugly
Technically, Clint Eastwood plays “The Good” in The Good, the Bad and the Ugly, but he’s a pretty hard-bitten bounty hunter who you just know has done some sketchy stuff in his past. He may not be the actually outlaw, but he’s not a true “white hat” either (though he does wear one, of course).
Eddington
One of the most interesting Westerns in recent years has to be Ari Aster‘s Eddington. It’s a little tricky to pick a true “outlaw” in this one, as Joaquin Phoenix is a lawman, which would traditionally be a white hat (as he wears in the movie). On the other hand, he murders some people in dramatic way, pushing him to the dark side. Still, at the end of the movie, you can’t help but sympathize with his plight.
Django Unchained
While traditionally Westerns have had very clear sides, the more modern iterations of the genre, like Django Unchained, blur the lines in the best way. Is Django (Jamie Foxx) good or bad? Well, clearly he’s both.
The Dirty Dozen
The best War movies and great Westerns often have similar DNA, and nowhere is this more obvious than in the classic The Dirty Dozen. Sure, it’s set during World War II, thousands of miles from the Old West, but in every other way it feels like a Western.
Hell Or High Water
While many modern Westerns blur the lines between good and bad, Hell or High Water, from director David Mackenzie and written by Taylor Sheridan, is clear. The outlaws, played by Chris Pine and Ben Foster, are on the run from a Texas Ranger (Jeff Bridges) after robbing a bank. It might be set in the 2010s, but it has a timeless Western quality.
Star Wars
Star Wars is part Sci-Fi classic, Part space, and yep, part Space Western. A ragtag group of outlaws fighting the establishment is the definition of a classic Western. There is no need to really explain a movie everyone has seen multiple times.
Ned Kelly
A young Heath Ledger leads a fantastic cast, including Orlando Bloom and Naomi Watts, in this 2003 Australian film about a legendary Australian outlaw, Ned Kelly, fighting back against prejudice in 19th Century Australia. It isn’t set in the American West, but it definitely belongs on this list. It’s also one of Ledger’s movies that many haven’t seen, but it shows just how great an actor he was at such a young age.
The Assassination Of Jesse James By The Coward Robert Ford
There is no more notorious outlaw in the Old West than Jesse James. In The Assassination Of Jesse James By The Coward Robert Ford, James is played by Brad Pitt, and the story of the end of his life is a spectacular example of a 21st-century Western.
The Magnificent Seven
Director John Sturges is the king of Hollywood Westerns, and The Magnificent Seven might just be his most beloved film. The outlaws are a who’s who of huge Hollywood names in 1960, including Steve McQueen, Yul Brynner, James Coburn, and Charles Bronson. It’s a stone-cold classic.
No Country For Old Men
Picking an outlaw in No Country for Old Men, like many modern Westerns, can be tricky. Obviously Anton Chigurh (Javier Bardem) is an easy choice, and you can make the argument that Llewelyn Moss (Josh Brolin) is the “good guy,” but no one in the movie is totally innocent, and we’re all rooting for Llewelyn, who has stolen a lot of money.
The Hateful Eight
Okay, let’s get real here, pretty much every character in The Hateful Eight is repugnant. I guess we’re supposed to be rooting for Jennifer Jason Leigh’s character, and she’s technically the outlaw here, so it’ll work for this list.
The Quick And The Dead
Sam Raimi’s The Quick And The Dead, starring Sharon Ston,e might be a nineties movie, but it definitely has the vibe of a classic Western. It’s also unique in the genre as the protagonist, the outlaw we’re rooting for, is a woman.
The Warriors
This is another stretch, sure, but in many ways, the cult classic The Warriors has all the elements of a great Western. A gang of outlaws gets on the wrong side of other outlaws and has to make a run for the border (or, in this case, Coney Island). What isn’t a “Western” about that? It’s one of the best cult classics of all time and a quintessential ’70s flick.
A Fistful of Dollars
There are a ton of classic Westerns starring Clint Eastwood that belong on this list, and A Fistful of Dollars is definitely one of them. This was the Spaghetti Western that really made the genre great, and is the first in the “Dollars” trilogy, along with For A Few Dollars More, and The Good, The Bad and the Ugly.
El Mariachi
Before he remade it as Desperado, Robert Rodriguez made his name with the low-budget indie El Mariachi. It follows the same story, but El Mariachi is much more raw in every way. It’s not as flashy, but that works in its favor. Westerns weren’t something that Indie filmmakers were making in the ’90s, so that makes this one extra special.
The Wild Bunch
Director Sam Peckinpah was known for his use of violence in his movies and was a real pioneer of 1970s cinema. One of his best, and most popular movies, has to be The Wild Bunch about a gang of outlaws at the tail end of the “Old West” trying to find their way in the early 20th Century. Like much of Peckinpah’s work, it’s a very different take on a classic genre.
Bonnie And Clyde
There are a lot of parallels between the Great Depression era and the Old West. Outlaws were folk heroes, and everyone rooted for them to take down the establishment. Clyde Barrow and Bonnie Parker are the quintessential example of that, and the 1967 movie based on their crimes, starring Warren Beatty as Barrow and Faye Dunaway as Parker, is a classic modern take on an old Western vibe.
Robin Hood: Prince Of Thieves
Long before there was a wild west, there was Sherwood Forest, where Robin Hood and his band of merry men fought the law, and most of the time, won. Robin Hood: Prince Of Thieves is maybe the best version of this ancient tale that closely resembles a Western.
Maverick
1994’s Maverick, starring Mel Gibson, Jodie Foster, and James Garner, is an adaptation of a ’50s TV show of the same name starring Garner. The movie is set on a riverboat during a poker tournament, and while there aren’t any cattle rustlers, it’s still a wonderful example of a Western where you root for the outlaw. Or outlaws in this case.
American Outlaws
Colin Farrell stars as Jesse James in American Outlaws, a Western from 2003 that hardly anyone remembers, but if you love movies about outlaws in the Old West, it’s a movie you’d probably enjoy. It’s not the best movie you’ll ever see, but it is a really fun Western
Pat Garrett And Billy The Kid
Sam Peckinpah made some really fun Westerns in the early ’70s, and recruiting Bob Dylan to not only have a role in the movie, but also provide some music (including his classic “Knockin’ On Heaven’s Door”), was a stroke of genius in Pat Garrett And Billy The Kid. The title pretty much gives the movie away, as it’s about the legendary lawman Pat Garrett’s (James Coburn) hunt for the outlaw Billy the Kid (Kris Kristofferson). Of course, you’re gonna root for Billy!
Silverado
Kevin Costner has starred in some great Westerns over the years, and his first, Silverado, is still one of his best. Costner plays a young gunslinger who gets involved with a gang of outlaws in this classic. The cast alone is worth the watch, including Kevin Kline, Rosanna Arquette, Scott Glenn, Danny Glover, Brian DennehyScott Glenn, Jeff Goldblum, and, in a surprisingly great performance, John Cleese.
The Long Riders
There are quite a few movies about Jesse James, but The Long Riders is unique because of the casting. The James brothers are played by real-life brothers Stacey and James Keach. The Younger brothers are played by David, Keith, and Robert Carradine. The Millers are played by Dennis and Randy Quaid, and the Fords are played by Nicholas and Christopher Guest. It’s super fun.
Young Guns II
We couldn’t leave Young Guns II off this list. Sure, it’s not as legendary as the first movie in the series, but in a lot of ways, it’s more fun. The cast is epic, and they are all clearly having fun making this sequel.
Smokey And The Bandit
There is nothing more classic in a Western than the outlaw wearing a cowboy hat trying to outfox and outrun the law while falling in love with a runaway bride. So, you tell me, is Smokey and the Bandit a Western? I say the answer is a resounding yes, even if the bandit has traded his horse for a Trans Am.
High Plains Drifter
After making his name in the Spaghetti Westerns of the 1960s, Clint Eastwood made one of his first American Westerns as a director with High Plains Drifter in 1973. It’s the second film he directed, and it led to a fantastic career as both star and director.
