Highlights

  • Clint Eastwood's Western films have become timeless classics, showcasing his stellar acting and directorial capabilities.
  • Some of Eastwood's Westerns, like Paint Your Wagon and Bronco Billy, demonstrate his ability to take on lighthearted and comedic roles.
  • Cry Macho, directed and starred in by Eastwood, marks a potential end to his Western career, offering a poignant and reflective portrayal of a character coming to terms with his past.

Clint Eastwood is undoubtedly an icon of the Western movie genre. His icy cold demeanor in the iconic The Man with No Name trilogy captivated audiences and solidified his role as a gun-slinging stalwart in Hollywood. Over the succeeding decades, Eastwood would add to his resume a stellar list of Western films that still stand the test of time.

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All of Clint Eastwood's Westerns have their merits, depending on the era in which it was made, the point it marks in Eastwood's career, and the viewer's taste. The best are often recognized as examples of Eastwood's stellar acting and directorial capabilities. When you're in the mood for a Western flick, any of these classic movies would be an excellent choice.

Updated on January 30, 2024, by Kristy Ambrose: Clint Eastwood's career in acting and directing is filled with success. His career has spanned no less than six decades and reached well beyond the Western genre. Although he stated he wouldn't act again after Million Dollar Baby in 2004, but did return on numerous occasions when the part was too good to turn down. In 2019, he directed Richard Jewell, a biographical crime drama about the security guard who foiled a bomb plot at the 1996 Atlanta Olympics. In 2021, Eastwood directed and starred in Cry Macho, one last outing in the Western genre he helped define.

15 Paint Your Wagon

A Young Eastwood Sings

paint your wagon 3 characters in hats
  • Role: Sylvester Newel, aka "Pardner"
  • Directed by: Joshua Logan
  • Release date: October 15, 1969
  • Distributor: Paramount Pictures

Although Clint Eastwood is most famous for playing intimidating, no-nonsense characters, the actor has been known to perform in more lighthearted roles, too. Paint Your Wagon, a Western musical about two prospectors hunting for gold is a famous example of Eastwood showcasing his comedic side.

The film also co-stars Lee Marvin, another actor not exactly known for playing warm and cuddly characters on screen. Putting the two stars together in a film that features plenty of musical numbers certainly doesn't lack entertainment value. Paint Your Wagon isn't the most serious Western in existence, but fans of the genre or old Hollywood musicals should get a kick out of it nonetheless.

14 Joe Kidd

The Revisionist Western Genre

Joe Kidd drinking a beer with a shotgun next to him
  • Role: Joe Kidd
  • Directed by: John Sturges
  • Release date: July 19, 1972
  • Distributor: Universal Pictures

Joe Kidd isn't the most memorable film on Clint Eastwood's resume, but it has a unique charm. It tells the story of a former bounty hunter, our hero Joe Kidd, who gets mixed up in a violent dispute between peasants and a wealthy landowner. It's a familiar story often depicted in the Western genre and the film does little to distinguish itself from the rest.

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Fans of Clint Eastwood will still enjoy his customary, steely determination in the face of adversity. Robert Duvall also brings his usual A-game playing the film's main antagonist. Nevertheless, Joe Kidd's by-the-numbers approach to the Western genre makes it among some of the weakest of the bunch.

13 Bronco Billy

A Modern Story In A Classic Setting

bronco billy clint eastwood doing rodeo in a western hat
  • Role: Bronco Billy McCoy
  • Directed by: Clint Eastwood
  • Release date: June 11, 1980
  • Distributor: Warner Bros.

This is an underrated Clint Eastwood film about a guy called Billy who runs a Wild West show, and it's all about his efforts to keep it relevant despite declining public interest in it. It risks becoming lost amid Eastwood's impressive western back catalog, but there's enough in this film to deserve a look.

It co-stars Sandra Locke who also appeared in several films alongside Eastwood, including The Gauntlet and Every Which Way But Loose. Fans of his other work in the Western genre will enjoy this film, but it doesn't quite hit the heights of some of his other work.

12 Cry Macho

A Reflective Look At 60 Years Of The Western Genre

cry macho clint getting out of a car, wearing a hat
  • Role: Mike Milo
  • Directed by: Clint Eastwood
  • Release date: September 17, 2021
  • Distributor: Warner Bros. Pictures

Cry Macho is a neo-Western that sees Eastwood portray a former rodeo star who is trying to reconnect a boy with his father in Mexico. It was Eastwood's last western and acting role. Ever since the turn of the century, Eastwood's acting roles were reduced and his preference was primarily directing.

Fans must watch this film to complete the Clint Eastwood Western journey. He rolls back the years with a nuanced performance that acts as the perfect send-off to his involvement in the Western genre.

This is a movie that doesn't have the gun-slinging and heroics of his earlier films in the genre. What it does possess is a reflective look at a character who is coming to the end of his life, and his attempts to make sense of what came before, whilst helping a young boy connect with his estranged father.

11 Hang 'Em High

A Flawed Hero Seeking Revenge

Jed Cooper wearing a cowboy hat, with a rope next to him
  • Role: Jed Cooper
  • Directed by: Ted Post
  • Release date: July 31, 1968
  • Distributor: United Artists

Hang 'Em High is a different kind of Western film involving Clint Eastwood. Unlike some of his other movies where he is nigh untouchable, Eastwood's character in Hang 'Em High is often quite vulnerable. He makes mistakes and even gets injured on several occasions.

Eastwood plays a new marshal who seeks to track down the gang that tried to lynch him. The movie can sometimes be a slow burn as his character, Jed Cooper, eventually tracks down his assailants one by one. It's worth watching Eastwood's portrayal of a very human and fallible gunslinger.

10 Pale Rider

A Modern Western With Occult Vibes

Preacher in a cowboy hat
  • Role: The Preacher
  • Directed by: Clint Eastwood
  • Release date: June 26, 1985
  • Distributor: Warner Bros.

Pale Rider is a fairly unique Eastwood western due to its religious, and even supernatural, motifs. The plot centers around the machinations of a greedy mining executive as he tries to unscrupulously eliminate all competition. Eastwood plays a mysterious character known only as "The Preacher" who comes to the rescue.

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There is a lot of interesting ambiguity in Pale Rider. The film implies that The Preacher is some sort of ghost or even a guardian angel. The final duel between Marshal Stockburn and this mysterious person suggests that the former had killed the latter at some point, judging by his apparent shock. It's an underrated Western that doesn't get enough love.

9 Two Mules For Sister Sara

A Mexican-American Collaboration

Two mules for sister sara Nun tending a distressed hogan
  • Role: Hogan
  • Directed by: Don Siegel
  • Release date: May 28, 1970
  • Distributor: Universal Pictures

Not all of Clint Eastwood's westerns were entirely gritty. Two Mules for Sister Sara adds periodic dashes of humor in just the right places. As usual, Eastwood plays a taciturn and hard-bitten drifter, who rescues a wayward nun on his travels and allows her to tag along.

The setting of the film is rather unique. It takes place during the French intervention in Mexico, and the subsequent domestic unrest it created. The movie's lighter tone compared to some of Eastwood's other films may not appeal to everybody. Nevertheless, the on-screen chemistry between Shirley MacLaine and Clint Eastwood is hard not to enjoy.

8 A Fistful Of Dollars

Eastwood's First Iconic Cowboy Role

The Man With No Name in a cowboy hat roughing someone up
  • Role: The Stranger
  • Directed by: Sergio Leone
  • Release date: January 18, 1967
  • Distributor: United Artists

The first entry in The Man with No Name trilogy, A Fistful of Dollars helped put Clint Eastwood on the map. Audiences witnessed for the first time Eastwood's trademark flick of the poncho before he subsequently guns down his opponents. The self-assured effortlessness he exudes in this film would become a familiar character trait for his future roles.

The plot of A Fistful of Dollars involves a deadly feud between two rival families. As a freelancer, The Man with No Name plays the rivals off against each other for his benefit. The iconic final duel at the end of the film against Ramon Rojo is difficult to forget.

7 Gran Torino

A Modern Western Set In Urban America

Gran Torino Walt sat on his porch with a beer
  • Role: Walt Kowalski
  • Directed by: Clint Eastwood
  • Release date: December 12, 2008
  • Distributor: Warner Bros.

Gran Torino isn't set against the backdrop of the wild frontier like a lot of Eastwood's previous forays into the Western genre. However, it is considered a contemporary Western, set in an Urban America that has fallen into disrepair under numerous failed governments.

Eastwood plays the grumpy Korean war veteran, Walt Kowalski, who is mourning the loss of his wife and must deal with his prejudices when interacting with his neighbors. He soon strikes up a bond with the family and protects them from a vicious gang in the area.

Eastwood returned to this role after announcing his retirement from acting and put in one of the best performances of his career. Not a typical Western, but one that is well worth a watch, and it adds context to a lot of Eastwood's other work in the genre.

6 The Outlaw Josey Wales

An Action Western Driven By Revenge

josey wales with two guns
  • Role: Josey Wales
  • Directed by: Clint Eastwood
  • Release date: June 30, 1976
  • Distributor: Warner Bros.

The Outlaw Josey Wales is an action-packed revenge tale set after the events of the American Civil War. Eastwood plays the eponymous outlaw in his quest to avenge the murder of his family. Along the way, he puts his twin Colt 1851 Navy revolvers to famous and deadly use.

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The film explores how the destructive legacy of the Civil War affected not only the land itself but its people as well. The death of Wales's family in the first place is fueled by the enmity between North and South. On a more surface level, the amount of satisfying action sequences makes the film highly enjoyable to watch.

5 High Plains Drifter

A Western That's Also A Ghost Story

The Stranger with a cowboy hat on, holding a cigar
  • Role: The Drifter
  • Directed by: Clint Eastwood
  • Release date: April 6, 1973
  • Distributor: Universal Pictures

Similar to Pale Rider, High Plains Drifter has seemingly supernatural overtones to it. However, whereas The Preacher is a force for good, The Stranger is bent on revenge. Eastwood's character aims to punish the residents of a small mining town for a past misdeed. It's only revealed gradually through flashbacks what exactly the townspeople have done.

It's quite a chilling tale, rich in both symbolism and metaphor. The audience slowly puts the puzzle pieces together in much the same way the townsfolk do on-screen. It would be a disservice to the reader to spoil anything else about the plot. It's best to experience it first-hand.

4 The Beguiled

A Story Of Psychological Horror In The South

Beguiled, John looking terrified
  • Role: Corporal John 'McBee' McBurney
  • Directed by: Don Siegel
  • Release date: May 28, 1971
  • Distributor: Universal Pictures

Eastwood aficionados shouldn't miss out on The Beguiled. Set during the American Civil War, a wounded Union soldier (Eastwood) takes shelter inside an all-female boarding school deep behind enemy lines. Mounting jealousy develops between the women as they compete for the affection of their unexpected guests.

The film relies less on traditional Western action, and more on the steadily boiling tension of a thriller. The Beguiled possesses plenty of twists and turns that should keep fans of both genres on the edge of their seats.

3 For A Few Dollars More

Revenge, Money, And Bounty Hunters

The Man With No Name with a cowboy hat on and cigar in his mouth
  • Role: Manco, aka The Man With No Name
  • Directed by: Sergio Leone
  • Release date: December 30, 1965
  • Distributor: United Artists

For a Few Dollars More is the second entry in The Man with No Name trilogy. This time around, Eastwood's mysterious loner is a bounty hunter looking to cash in by eliminating a violent band of outlaws. He faces stiff competition from Douglas Mortimer, played by Lee Van Cleef, a rival bounty hunter after the same gang.

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Seeing Clint Eastwood and Lee Van Cleef on the screen together is always great. Van Cleef was a big draw for the Spaghetti Western genre in his own right. It's a film with few slow moments as the motivations of all the key players are gradually revealed. The explosive finale also dishes out some satisfying payoffs.

2 Unforgiven (1992)

Just When He Thought He Got Out

Munny pointing a shotgun in a bar
  • Role: Will Munny
  • Directed by: Clint Eastwood
  • Release date: August 7th, 1992
  • Distributor: Warner Bros.

Directed by Clint Eastwood himself, Unforgiven tells the story of a notorious former outlaw who gets drawn back into his old ways. Repentant for his past actions, but struggling to live a normal life, William Munny embarks on a bounty-hunting mission to save his failing ranch.

The plot of Unforgiven is simple but poignant. It explores the idea of what it means to be redeemed and whether such a thing is even possible. The film shows how frighteningly quickly Will Munny can regress to his former self when the situation demands it. Gene Hackman, Morgan Freeman, and Clint Eastwood are at their finest in this movie.

1 The Good, The Bad And The Ugly (1966)

It Could Be The Greatest Western Of All Time

close up on blondie with a cowboy hat on
  • Role: Blondie, aka The Man With No Name
  • Directed by: Sergio Leone
  • Release date: December 23, 1966
  • Distributor: United Artists

One of the greatest Westerns of all time, The Good, the Bad, and the Ugly is the final entry in "The Man with No Name" trilogy. Three men race to discover hidden Civil War gold buried in an isolated cemetery. Alliances between the men are made and broken multiple times along the way.

The final standoff at the end of the film is a piece of cinematic history. To this day, the ending scene is still often imitated in other films and media. Lee Van Cleef and Eli Wallach deliver superb performances as The Man with No Name's vicious rivals. Regardless of the genre, The Good, the Bad and the Ugly is a masterpiece of filmmaking that still stands the test of time.

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