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Film

The 10 best Clint Eastwood directed movies

@Russellisation

There are few actors that hold the same cinematic majesty as Clint Eastwood, the mystic western ‘man with no name’ and an actor widely considered to be one of the biggest stars of 20th-century filmmaking. A hugely influential actor known for Sergio Leone’s spaghetti western trilogy, including the A Fistful of Dollars, For a Few Dollars More and The Good, the Bad and the Ugly, Eastwood has since also enjoyed considerable success behind the camera. 

Though he is well-known in front of the camera, it’s easy to forget just how many films Clint Eastwood has directed, helming over 30 feature films, ranging from classic westerns to modern Oscar winners. Taking home the Academy Award for Best Picture in 2004 for his boxing drama Million Dollar Baby as well as his revisionist western Unforgiven, Eastwood has earned his fair share of critical praise. 

Having been in the industry for over half a century, Eastwood is a veteran of Hollywood cinema both in front of and behind the camera. Take a look at our list of the filmmaker’s ten very best directorial feats below, from his vital contributions to the western genre to his personal crime stories that almost always star him in the leading role. 

The top 10 Clint Eastwood directed movies

10. Bird (1988)

As a longtime lover of Jazz, Eastwood ran with his passion for his 1988 biopic Bird, retelling the troubled life and career of the musician Charlie ‘Bird’ Parker. Played by Forest Whitaker, who won a Cannes Best Actor award for his performance, Parker’s story is a tragic one that is compellingly told with genuine compassion by Eastwood and the film’s screenwriter, Joel Oliansky. 

Distinguishing the film from the many other music biographies is Eastwood’s own personal love and knowledge of the art form, conducting the film with a frenetic, sometimes erratic style that reflects the music itself. 

9. Gran Torino (2008)

A fan favourite upon its release, Eastwood’s 2008 release Gran Torino may be his most liked film of the 21st century. Starring himself in the lead role, the actor/director plays a disgruntled Korean War veteran who sets out to help change the lifestyle of his teenage neighbour, an immigrant who previously tried to steal his beloved 1972 Gran Torino. 

A drama spiked with moments of action, Eastwood’s commercial success also spoke to a reality of racial intolerance, with the film being a lot more compelling than its marketing suggested.

8. Mystic River (2003)

A complex two-hour drama, Mystic River tells the story of three men, once childhood friends, whose lives are thrown into disarray after one of them has a family tragedy. Based on Dennis Lehane’s mystery novel of the same name, Eastwood’s film stays loyal to the book whilst adding its own flourishes, largely coming from the characterisation of the three lead roles.

Armed with an all-star cast, including the likes of Sean Penn, Tim Robbins, Kevin Bacon, Emmy Rossum, Laurence Fishburne and Laura Linney, Mystic River swooped two awards for Best Leading and Best Supporting Actor at the 2004 Academy Awards.

7. Pale Rider (1985)

Clint Eastwood directed several westerns during his time as a filmmaker, and whilst the 1985 movie Pale Rider wasn’t his very best, it remains an underrated genre piece. Telling the story of a mysterious preacher who protects a humble mining village from a greedy company trying to take their land, Eastwood proved, not that he still needed to, that he was one of the western genre’s most powerful stars. 

Appearing alongside the likes of Richard Kiel and Chris Penn, Eastwood creates a thrilling drama that goes light on the action in favour of something calmer and arguably cooler. 

6. The Bridges of Madison County (1995)

Based on Robert James Waller’s 1992 novel of the same name, The Bridges of Madison County, released in 1995, almost proved to be as commercially and critically successful as the beloved book itself. Starring in the film alongside Meryl Streep, Eastwood plays a photographer in the 1960s who wanders into the life of a humble housewife for four days and changes her perspective on life. 

A charming love story, the film earned Streep her tenth Oscar nomination and enjoyed a respectable run at the box office despite it being a change of course for Eastwood’s often violent films.

5. High Plains Drifter (1973)

Only Eastwood’s second directorial effort, High Plains Drifter was released at the very height of the actor’s popularity, merely two years after the crime thriller Dirty Harry. A critical darling, High Plains Drifter tells the story of a mysterious stranger who is persuaded by a town to defend them against a vicious trio of crooks, showing just how much the figure of Eastwood is respected out in the wild west. 

A style statement of intent, Eastwood’s 1973 film is an allegorical treat that takes liberties from such classics as Akira Kurosawa’s Seven Samurai in its epic, almost biblical, tone.

4. Million Dollar Baby (2004)

Taking home the award for Best Picture in 2005, 11 years after his previous award winner Unforgiven, Million Dollar Baby remains a rousing watch to this very day, following the tumultuous life of a determined woman working to become a professional boxer. Winning Hilary Swank an Oscar for her leading performance, her powerful role is bolstered by the supporting actors of Morgan Freeman, Anthony Mackie, Jay Baruchel and Eastwood himself.

An emotional sports drama that diverts down alleyways you could never predict from the outset, Eastwood subverts the sports movie and provides a compelling story about the death of a dream.

3. Letters from Iwo Jima (2006)

In a move that has yet to have been replicated by any other filmmaker, Eastwood created two movies in 2006 about World War II’s Battle of Iwo Jima, one from the Japanese perspective, and the other from the American. Whilst the American film, Flags of Our Fathers was a little formulaic, Letters from Iwo Jima proved to be a powerful piece of cinema, earning Eastwood a Best Picture nomination in 2007. 

Painting a sympathetic portrait, this compelling film provides a crucial secondary point of view on the WWII battle that simply works to further highlight the folly of war itself.

2. The Outlaw Josey Wales (1976)

An overlooked gem of western cinema, The Outlaw Josey Wales is Clint Eastwood’s best performance in the genre outside of Sergio Leone’s iconic Dollars trilogy. Playing the title character, the 1976 film tells the story of Josey Wales’ mission for revenge after his wife and son are murdered by pro-Union Army soldiers. A brutal revenge story done right, Josey Wales would later become one of Eastwood’s most iconic characters.

With deft direction from Eastwood and some thrilling cinematography, The Outlaw Josey Wales comes to life during its action scenes, though remains compelling throughout. 

1. Unforgiven (1992)

Only one of four Western films ever to take home the Oscar for Best Picture, Unforgiven would become known as one of the greatest revisionist films of modern cinema. Questioning the role of the American psyche in the creation of an unfavourable contemporary culture, Eastwood’s film holds an enduring appeal, with the director starring as a merciless killer turned pig farmer who is forced to return to his life of crime.

Analysing the place for the Western caricature in modern life, the film is a fascinating analysis of the genre, breaking down its sheer identity to understand how it reflects the culture and ideals of a changing America.