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14 Best Clint Eastwood Movies Of All Time

14 Best Clint Eastwood Movies Of All Time

This 91-year-old movie legend continues to star and direct his own films. Here are some of Clint Eastwood's best works throughout the decades.

Clint Eastwood is a true living legend. The movie star is about to release his latest neo-Western film, 'Cry Macho' at 91 years old!

Eastwood has been working in the film and television industry for over 70 decades now, but his on-screen presence never fades. He's worn many hats (pun intended) since his early days as a spaghetti western icon up to this date.

In celebration of his upcoming movie, 'Cry Macho,' we compiled this special list as a tribute to Eastwood's cinematic legacy.

Here are the 14 of the best Clint Eastwood films of all time.

'A Fistful of Dollars'

FISTFUL OF DOLLARS (1964)

Italian director Sergio Leone was looking for an actor to lead the Western “homage” to the Japanese movie 'Yojimbo.' He initially wanted Henry Fonda to play the "Man with No Name." However, the production company could not afford his talent fee. The role was later offered to Charles Bronson,  Rory Calhoun, Henry Silva, Tony Russel, Steve Reeves, Ty Hardin, and James Coburn. They all turned down the project.

Leone reached out to Richard Harrison, who starred in the first Italian western, Duello nel Texas. Harrison rejected the role, too. But he recommended Clint Eastwood instead.

The recommendation led to one of the best decisions in movie history. 

At that time, Eastwood was also tired of playing the good conventional good guy in 'Rawhide.' He decided that it is about time he plays an anti-hero role. 

Eastwood would later become the archetypal anti-hero, the "Man With No Name." He inserts himself between two rival factions in a small country town and introduces himself as an assassin for hire to both parties. He earns twice the money while watching both parties destroy each other.

The film was a massive success, ushering in a new era in cinematic history. The film later spawned two sequels, 'For a Few Dollars More' and 'The Good, the Bad and the Ugly.'

In 1967, three years after the Italian release, the film made its way into the United States with the rest of the "Dollars Trilogy."

'A Fistful of Dollars' was significant both to Eastwood and director Leone. The film gave birth to a genre later named "Spaghetti Westerns," a term the American critics coined because most Westerns are created and directed by Italians.

'FOR A FEW DOLLARS MORE'

FOR A FEW DOLLARS MORE (1965)

The sequel to 'A Fistful of Dollars,' 'For a Few Dollars More' further established Eastwood's name into stardom. Eastwood reunites with director Sergio Leone in another epic film filled with angst and iconic duels. 

Eastwood reprises his role as the "Man With No Name" AKA Manco. He teams up with another bounty hunter Col. Douglas Mortimer (Lee Van Cleef), to take down a criminal outlaw known as El Indio (Gian Maria Volonte).

THE GOOD, THE BAD AND THE UGLY 

THE GOOD, THE BAD AND THE UGLY (1967)

The third film in the "Dollars Trilogy", 'The Good, the Bad and the Ugly is considered the greatest of spaghetti westerns. 

The film follows three gunslingers: Clint Eastwood as "the Good", Lee Van Cleef as "the Bad", and Eli Wallach as "the Ugly." The three are chasing down a missing cache of Confederate gold in the middle of a violent and chaotic Civil War. The film ends with one of the most epic showdowns in film history. 

COOGAN'S BLUFF

COOGAN'S BLUFF (1968)

'Coogan's Bluff' marks the next chapter of Eastwood's acting career. It established his new persona after years of working with Leone.

In 'Coogan's Bluff,' Eastwood plays a veteran deputy sheriff from a rural county in Arizona. He goes to New York City to arrest a fugitive named Jimmy Ringerman. 

'Coogan's Bluff' is the first collaboration between acclaimed director Don Siegel and Eastwood. The two would later work together in four more films namely: 'Two Mules for Sister Sara' (1970), 'The Beguiled' (1971), 'Dirty Harry' (1971), and 'Escape from Alcatraz' (1979).

Quentin Tarantino would later call the film "a trial run for the next twenty years of action cinema."

DIRTY HARRY

DIRTY HARRY (1971)

'Dirty Harry' is the film that turned Eastwood into a macho screen icon. 

Clint Eastwood plays Officer Harry Callahan, a cop willing to do “every dirty job that comes along.” He tracks down a psychopath terrorizing the City by the Bay. 

Dirty Harry became so popular that Eastwood would bring him back four more times, including in 1983’s 'Sudden Impact,' where the iconic line “Go ahead, make my day" came.

HIGH PLAINS DRIFTER

HIGH PLAINS DRIFTER (1973)

After his successful stint with Leone in the 60s, Eastwood returns to his Western roots. 

This time, he is not just a star but a director too. 

Eastwood plays a mysterious stranger. The government hires him to protect the town from ex-convicts plotting revenge after getting sent to prison for a crime they did not commit.

The film was a massive success, proving that Eastwood can work magic both in front and behind the camera.

THE OUTLAW JOSEY WALES 

THE OUTLAW JOSEY WALES (1976)

'The Outlaw Josey Wales' is one of Eastwood's most iconic roles in cinematic history. 

Directed by Eastwood himself, 'The Outlaw Josey Wales' tells the story of an eponymous Missouri farmer. He seeks revenge after the Union militants murdered his family during the Civil War. 

Wales joins a Confederate guerrilla band and quickly becomes one of the most notable gunfighters. When the war ended, all the fighters surrendered to the Union officers, except Josey. Those who surrendered eventually get murdered. Josey becomes an outlaw trying to build a new life while the Union and bounty hunters continue to trail him.

ESCAPE FROM ALCATRAZ

ESCAPE FROM ALCATRAZ (1979)

Inspired from the real-life 1962 prisoner escape from the maximum-security prison on Alcatraz Island, 'Escape From Alcatraz' stars Clint Eastwood as notorious convict Frank Marshall. Marshall has busted out of prison a few times. When he arrived in Alcatraz, the warden tells him that no one has ever escaped Alcatraz, and no one ever will. 

But Marshall is about to prove them wrong. 'Escape From Alcatraz' is a 1 hour and 47 minutes of thrill, and one of the best prison break films in history. 

The film is the fifth and final collaboration between Siegel and Eastwood. 

HONKYTONK MAN

HONKYTONK MAN (1982)

Clint Eastwood shares the screen with his son Kyle Eastwood in this fantastic musical drama set in the Great Depression. Aside from taking the lead role, Clint Eastwood also serves as the film director and producer. 

'Honkytonk Man' is miles away from his previous films that thrive in chaos and violence. It follows a Dust Bowl singer-songwriter named Red Stovall (Clint Eastwood), who dreams of playing the Grand Ole Opry. His nephew (played by Clint’s son, Kyle) comes up with him and helps compose the song that could lead him to success. 

Sadly, Red is also suffering from Tuberculosis. The fatal disease has reached its final stages. Although he managed to score a recording session from companies, TB eventually took his life.

The 'Honkytonk Man' is a poignant story loosely based on the life of country legend Jimmie Rodgers.

PALE RIDER

PALE RIDER (1985)

'Pale Rider' is another masterpiece written, directed, and starred by Clint Eastwood. 

Around this time, people are already getting tired of Western movies, but Eastwood decided to do one anyway. 

Eastwood plays a mysterious stranger who rides into a town where a mining tycoon is threatening the livelihood of small-time contractors. He quickly became the town's gun-toting local guardian angel. 

The film grossed nearly $41 million at the box office and became the highest-grossing Western of the 1980s. It shows that people do not mind seeing another Western as long as Eastwood is in it.

'Unforgiven'

UNFORGIVEN (1992)

Clint Eastwood plays William Munny, an aging outlaw, and killer who leaves his farm to take one last bounty job.

He recruits an old friend (Morgan Freeman) and joins “the Scofield Kid” (Jaimz Woolvett) to track a murderer on a bounty mission. 

The film brought home several accolades, including the Oscars for Best Picture, Best Director, Best Supporting Actor (for Hackman), and Best Editing. Eastwood was also nominated for Best Actor but lost to AL PACINO for his role in 'Scent of a Woman.'

IN THE LINE OF FIRE

IN THE LINE OF FIRE (1993)

In this 1993 thriller film, Clint Eastwood plays a Secret Service Agent Frank Horrigan. Horrigan is suffering from enormous guilt after failing to protect John F. Kennedy during his assassination. 

One day, he receives a call from "Booth," who tells Horrigan that he will kill the President. Despite his age, Horrigan returns to serve in the Presidential Protective Detail. "Booth" would use Horrigan's guilt and failure to taunt him continuously. Horrigan eventually gets his redemption after successfully saving the President this time. 

The film received favorable reviews. Kenneth Turan of LA Times calls it "crisply entertaining" adding that "every part of this film trades so heavily on Eastwood’s presence that it is impossible to imagine it with anyone else in the starring role."

Million Dollar Baby

MILLION DOLLAR BABY (2004)

Eastwood plays Frankie Dunn, an aging manager who trains Maggie Fitzgerald (Hilary Swank) in the boxing ring. It's a heartwarming tale of what Eastwood calls “a surrogate father-daughter love story.” 

'Million Dollar Baby' was a heart-pinching melodrama in itself, but the drama happening behind the camera is just as equally noteworthy. 

Several studios rejected the project, even after Eastwood signed up as an actor and director. Even Warner Bros, who had been Eastwood's partner for a long time, would not give him the US$30 million budget. 

Eastwood asked Lakeshore Entertainment's Tom Rosenberg to finance half the budget and handle foreign distribution. Warner Bros. contributed the remaining $15 million. 

The film went on to win Multiple Oscar, including Best Picture. 

The Mule

THE MULE (2018)

Clint Eastwood was already 88 years old when he starred and directed 'The Mule,' a crime drama film about a 90-year-old drug mule to the Mexican cartel. 

Eastwood plays Earl Stone, a horticulturist who does not have the best relationship with his family. For many years, he has put work above his family, and their relationship eventually falls out.

Frank's house is getting foreclosed. His business is down, and his daughter will not speak to him. 

He comes across a Mexican drug cartel that hires him to deliver their packages. At first, he didn't know that he was being used as a drug mule. When he finds out, dire circumstances arrises, and he gets forced to continue doing the illegal task. 

Along the way, he imparts some valuable lessons to the lives of the cartel members and finds redemption with his own life, too. 

'The Mule' grossed $173.6 million worldwide against a production budget of $50 million. It was highly praised and commercially successful. It could have been a decent film to retire to. However, Clint Eastwood proves that age is just a number, and he is not planning on retiring just yet.

Now, at 91 years old, Clint Eastwood is about to release another neo-Western drama film starred, directed, and produced by himself. The film titled 'Cry Macho' will hit the theaters on September 17, 2021. Read our preview here to find out more. 

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