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
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.
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.
Morgan Freeman and the late Gene Hackman, this Best Picture-winning film is a true masterpiece.
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.
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.
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, blur the lines in the best way. Is Django (Jamie Foxx) good or bad? Well, clearly he’s both.
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.
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.
shows just how great an actor he was at such a young age.
quintessential ’70s flick.
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!
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.