16 best Clint Eastwood movies you should watch

By Alex Wiggan

Whether you’re a fan of war pictures, Westerns, gritty crime thrillers, action movies, or everything in between, the chances are at some point in your life you’ve stumbled across the work of US actor, Clint Eastwood. Since moving into the film industry in the 1950s, Eastwood has been a huge part of the movie landscape, leading countless pictures and picking up a legion of fans in the process.

Across the course of many decades, Eastwood has entertained the masses with his cool attitude, his steely gaze, and his no-nonsense characters. This in turn has led to significant commercial success, as well as a portfolio of impressive titles.

Today I want to cast the spotlight on Clint Eastwood with a look back at his many highlights. During his time on screen Eastwood has delivered a string of hit movies, and I want to place the focus on the best of the best with a rundown of his top films.

Below you will find a collection of the best Clint Eastwood movies that you really should watch. These are the movies to pop on your watchlist, because they showcase Eastwood on top!

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Where Eagles Dare (1968)

First up is the action-adventure war thriller, Where Eagles Dare. The movie – directed by Brian G. Hutton – was released in 1968 and follows the story of a team of Special Operatives, who attempt to save a captured US General from the Schloß Adler fortress.

Set during World War II, Eastwood took on the role of Lt. Morris Schaffer for this picture, which would become a fan-favourite. Filled with action and stunning cinematography, Where Eagles Dare is a thoroughly entertaining movie and it was a huge success at the box-office back in ’68.

Gran Torino (2008)

Next up is the 2008 drama, Gran Torino – a movie which pits an aged Eastwood against much younger antagonists. In this film, Eastwood takes on the role of recently widowed Korean War veteran Walt Kowalski, who is forced to defend himself and one of his young neighbours from a vicious gang.

As well as starring in Gran Torino, Eastwood also directed and co-produced the picture. The movie was another big success, taking $270 million from a budget of around $30 million, and was a hit with the critics too.

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Play Misty For Me (1971)

Movie three on this list goes to the 1971 psychological thriller, Play Misty for Me – another movie directed by Eastwood. For those who have let this film pass them by, Play Misty for Me tells the story of a radio disc jockey who becomes stalked by an obsessed fan.

In the film, Eastwood takes on the role of Dave Garver – a successful DJ who broadcasts a nightly show across the airwaves in the city of Carmel-by-the-Sea. Garver’s biggest fan is Evelyn Draper, a woman he initially develops a relationship with, but it quickly becomes clear she is frighteningly unhinged and worryingly deadly!

Dirty Harry (1971)

Of all the movies on this list, this next film, 1971’s Dirty Harry is arguably the most famous of them all. And it’s famous for all the right reasons, as Dirty Harry is without doubt one of Clint Eastwood’s all-time greats.

Directed by Don Siegel, the film follows the story of San Francisco Police Inspector, ‘Dirty’ Harry Callahan as he finds himself on the trail of a psychopathic sniper known as Scorpio. In the film, Callahan has to track down Scorpio as quickly as possible, before the bodies begin to pile high.

Featuring smart direction, superb cinematography, a magnificent script, and an excellent performance from Eastwood, Dirty Harry is top notch and nothing less. The film was another big hit at the box-office, spawning a series of sequels which included Magnum Force (1973), The Enforcer (1976), Sudden Impact (1983), and The Dead Pool (1988).

Magnum Force (1973)

As noted above, the critical and commercial success of Dirty Harry led to further instalments, which initially continued with Magnum Force – a sequel which more than deserves to be on this list. Directed by Ted Post, Magnum Force sees Harry Callahan on a new case which this time involves rogue police officers.

In the film, a collection of San Francisco motorcycle cops take the law into their own hands and start dispensing deadly justice. This causes Callahan to face a threat from within the system, which also puts him in the firing line.

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A Fistful of Dollars (1964)

Image: ©Jolly Film/Constantin Film/Ocean Films

Onto movie number six on this list and it is yet another iconic picture. The film is the 1964 spaghetti Western, A Fistful of Dollars.

Directed by Sergio Leone, A Fistful of Dollars saw Eastwood take on the lead role of ‘the man with no name’ – a gun-slinging stranger who arrives at a little town on the Mexico-US border. In the movie, the stranger gets caught up in a feud for control of the town, and proves he is more than equipped to handle himself.

As with Dirty Harry, A Fistful of Dollars provided Eastwood with a signature role and is regarded as the film which pretty much kick-started his big run of Westerns. A Fistful of Dollars was accompanied by two sequels – A Few Dollars More (1965) and The Good, the Bad and the Ugly (1966) – which are also damn fine films (and probably should be on this list).

The Outlaw Josey Wales (1976)

Clint Eastwood pulls double duties on this next film, hopping in the director’s chair while also starring as the titular Josey Wales – a Missouri farmer who becomes an outlaw. In the film, Wales joins a Confederate guerrilla band following the murder of his family, but soon becomes the target of Union soldiers and bounty hunters after he decides to make a new life for himself.

Set during the American Civil War, The Outlaw Josey Wales is another one of Eastwood’s hit Westerns. The movie was well received by critics upon release, and became a financial success.

The Gauntlet (1977)

Up next is the action-thriller, The Gauntlet. Directed by and starring Clint Eastwood, The Gauntlet is essentially a Dirty Harry movie which isn’t actually a Dirty Harry movie.

In the film, Eastwood plays the role of alcoholic cop, Ben Shockley, who is tasked with transporting a supposedly unimportant witness from Las Vegas to Phoenix. But as Shockley soon discovers, the witness is far more important than anyone will admit to, and someone is keen to bump her off.

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Kelly’s Heroes (1970)

Directed by Brian G. Hutton, Kelly’s Heroes is a comedy-drama, set during the events of World War II. Eastwood takes on the role of the eponymous Kelly, opposite a cast which includes Telly Savalas, Don Rickles, Donald Sutherland, and Gavin MacLeod, in a film about a crew of American GIs who go AWOL while attempting to steal from a French bank located behind German lines.

Escape from Alcatraz (1979)

Adapted from the 1963 book of the same name by J. Campbell Bruce, and based on a real-life event from 1962, Escape from Alcatraz is an action thriller from director Don Siegel. The film tells the story of Frank Morris – a criminal who along with fellow inmates, John and Clarence Anglin, made an escape from the maximum security prison on Alcatraz Island.

High Plains Drifter (1973)

Back to Westerns for this next film – the 1973 movie, High Plains Drifter. Directed by and starring Eastwood, the movie follows the story of a mysterious stranger who deals out justice in a corrupt mining town.

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Pale Rider (1985)

Sticking with Westerns directed and starring Eastwood, the next entry on this list goes to Pale Rider. Released in 1985, Eastwood plays the role of a mysterious preacher who protects a village from a greedy mining company intent on encroaching on their land.

Million Dollar Baby (2004)

Moving onto the next film on the list, which is the 2004 sports drama, Million Dollar Baby. Directed by and starring Clint Eastwood, alongside a cast which includes Hilary Swank and Morgan Freeman, Million Dollar Baby follows the story of an amateur boxer who is transformed into a professional sportswoman thanks to the help of an underappreciated boxing trainer.

Released to critical acclaim, Million Dollar Baby was a big hit with the critics back in ’04 and was a box-office success too. The film then went on to be nominated for multiple accolades, picking up four Academy Awards including Best Picture, Best Director (Eastwood), Best Actress (Swank) and Best Supporting Actor (Freeman).

Two Mules for Sister Sara (1970)

Don Siegel directs this next film – a Western about an American mercenary and a nun. Clint Eastwood takes on the role of Hogan, while Shirley MacLaine plays the titular Sister Sara.

Every Which Way But Loose (1978)

Almost at the end of the list, but there’s still time to fit in a beloved action comedy, and another one of Eastwood’s most memorable pictures – even if it is largely because of his co-star. The film is Every Which Way But Loose – a movie in which Eastwood acted opposite an orangutan named Clyde.

James Fargo directs this picture, which sees Eastwood play trucker and bare-knuckle brawler, Philo Beddoe. And while the movie was not well-received by critics upon release, it was a financial success and remains a popular entry in Eastwood’s portfolio.

Unforgiven (1992)

And finally, back to Westerns for this next picture, which was directed by, produced, and starred Clint Eastwood. The film is 1992’s Unforgiven, a film about an aging outlaw who takes on one final job, years after he gave up violence and turned his hand to farming.

Similar to the aforementioned Million Dollar Baby, Unforgiven was nominated for multiple accolades following its release and won four Academy Awards. The trophies included Best Director (Eastwood), Best Supporting Actor (Hackman), Best Film Editing (Joel Cox), and the much coveted Best Picture award.

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Recap

So, those are the sixteen best Clint Eastwood movies. Now, to save you from having to scroll back up, here are the titles of all the movies in one handy list!

Where Eagles Dare (1968)
Gran Torino (2008)
Play Misty For Me (1971)
Dirty Harry (1971)
Magnum Force (1973)
A Fistful of Dollars (1964)
The Outlaw Josey Wales (1976)
The Gauntlet (1977)
Kelly’s Heroes (1970)
Escape from Alcatraz (1979)
High Plains Drifter (1973)
Pale Rider (1985)
Million Dollar Baby (2004)
Two Mules for Sister Sara (1970)
Every Which Way But Loose (1978)
Unforgiven (1992)

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Editor/writer/action hero

Alex Wiggan

Alex is the writer and editor of It’s A Stampede! – a blog which specialises in movies, TV, comics, retro toys, and general geekery. He is a championing voice in nerd content, an expert in pop culture, and a trusted movie critic who publishes new reviews on a weekly basis. After graduating with a degree in film & television studies from the University of Derby in the UK, Alex went on to study journalism in Sheffield, before acquiring NCTJ accreditation. Prior to creating It’s A Stampede!, Alex was a magazine editor, a senior copywriter, a features writer, and a freelancer.

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