Ranking Clint Eastwood’s 10 Greatest Directorial Efforts

Clint Eastwood’s films – the ones he directs anyway – ebb and flow in odd ways over time. Typically, his films are lauded, awarded, celebrated as masterworks when they are first released. But time dilutes their impact more so than any other director’s works. Recently, however, save for the divisive but popular (and subpar) American Sniper, Eastwood has been struggling.

Think about the impact of Million Dollar Baby in 2004, the Best Picture winner that year; with 2016 eyes, the boxing drama has faded from the national consciousness, slotted as a decent but somewhat cloying story. The same fate met his one-two punch of Flags of Our Fathers and Letters from Iwo Jima. More recent efforts (Jersey Boys, anyone? J. Edgar?) have been simple bores.

To be honest, it’s been about a decade since Clint Eastwood’s work behind the camera has had any true staying power. But, of Eastwood’s 35 films he’s directed (this weekend’s Sully is #35), the quality far outweighs the mediocrity. From thrillers to westerns to wallops of undeniable dramatic intensity, here are Clint Eastwood’s 10 greatest films as a director.

Clint Eastwood

10. The Eiger Sanction (1975) – Eastwood’s fourth film as director focuses on an art professor who also happens to be a hired assassin. No, it isn’t based on a true story (or is it?!). This is one of his only forays into some sort of espionage thriller, as his Professor Hemlock must take a job where he winds up in Switzerland trying to find a Russian killer. The plot is infinitely more muddled than that, but it remains something altogether unique from the rest of Eastwood’s subdued catalogue in its globetrotting scope and adventurous spirit.

Clint Eastwood

9. Heartbreak Ridge (1986) – Clint Eastwood fits the hard-living Marine gunnery sergeant character better than just about anyone this side of R. Lee Ermey. Heartbreak Ridge fits Eastwood’s grizzled persona and, while it might fall into typical storytelling rhythms – rough drill sergeant has to whip cocky kids into shape – the film has authenticity coursing through its veins. The rough-natured boy club of the military, coupled with the energy and tension among so many well-constructed characters, elevate a standard plot.

Clint Eastwood

8. Million Dollar Baby (2004) – Yes, Million Dollar Baby is cloying and it eventually drowns in melodrama. And yes, it’s a boxing movie, the most worn sports genre in cinema history. And yet, Eastwood’s direction, his starring turn as Frankie Dunn – reluctantly (always) taking female boxer and white-trash offspring Maggie under his wing – still pulls us in. We can see certain twists and turns coming a mile away, but this film still manages to throw around some of its emotional weight in spite of its generic DNA.

Clint Eastwood

7. The Bridges of Madison County (1995) – I know my father wasn’t the only old man suckered into seeing this movie with their wives under the guise that “it’s a Clint Eastwood movie.” This is something entirely different than what pops expected; zero bullets are fired. Eastwood pulls way back, adapting Robert James Waller’s novel of heartbreak and longing, with a patient, loving eye. He and Meryl Streep star, and the brief respite they share in the middle of their predetermined lives is wonderfully light and eventually soul crushing.

Clint Eastwood

6. Absolute Power (1997) – On the heels of Madison County, Eastwood returned to the thriller genre with one of the most under appreciated political/heist thrillers in the subgenre. Eastwood plays an expert jewel thief who, wait for it, is estranged from his daughter and family. On a job one night, he witnesses the Secret Service murder a woman with whom the president is having an affair. Gene Hackman oozes evil as the president, and the duo of Dennis Haysbert and Scott Glenn are perfect as Secret Service agents. Eastwood’s film begins with an enrapturing murder scene, then builds from there.

Clint Eastwood

5. Play Misty for Me (1971) – Clint Eastwood’s directorial debut encapsulates everything that works about him behind the camera, especially in thrillers. He again stars, this time as a radio deejay who, after having an affair with an adoring fan (Jessica Walter, terrific), winds up in a whole heap of trouble. A precursor to Fatal Attraction, Play Misty for Me exists on the razor’s edge of incredible tension, yet it still manages to stay within itself without ever spinning out of control.

Clint Eastwood

4. The Outlaw Josey Wales (1976) – Even if it didn’t have that kickass poster, The Outlaw Josey Wales would be one of Clint Eastwood’s three or four greatest westerns. Joey Wales is a Missouri farmer and Civil War veteran who must leave his new peaceful life behind to avenge the death of his family; he also happens to be wanted man. Eastwood’s familiarity with the genre is on display in his second western as a director – the first being High Plains Drifter – as he manages to perfectly balance the dramatic moments with the intense action.

Clint Eastwood

3. Mystic River (2003) – Some may dismiss Mystic River as another Eastwood melodrama, but for me this will forever be a powerful drama filled to the brim with unforgettable performances. Sean Penn leads the charge as Jimmy, a man ripped apart by the murder of his teenage daughter. His childhood friend, Dave (Tim Robbins), is a suspect, and another, Sean (Kevin Bacon), the investigating officer. The fact that these three men share a childhood polluted by the abduction and sexual assault of Dave deepens the text of the film, and pulls us further into the way all of these men’s lives have been destroyed over time. But in the middle of this boy’s tale, let us not forget the incredible performances from Laura Linney, channeling Lady Macbeth, and Marcia Gay Harden, as Dave’s troubled, uncertain wife.

Clint Eastwood

2. A Perfect World (1993) – In the wake of Unforgiven’s success, Eastwood snuck in a quiet little masterpiece in the fall of ’93. Kevin Costner’s escaped convict, Butch, builds a surprising paternal relationship with his young “hostage,” Phillip/Buzz, and the pursuit of Eastwood, Laura Dern and federal marshals build and ominous road to reckoning. While the tension is terrific in A Perfect World, the relationships between its central players is the real draw. Eastwood captures the texture and sprawling openness of mid-century Texas, and shows us the inner turmoil of the characters with subtle beauty.

1992-Unforgiven-04

1. Unforgiven (1992) – It’s fitting that Clint Eastwood’s greatest achievement both in front of and behind the camera would be a deconstruction of the very genre which created his legend. Unforgiven is not an anti-western as so many people claim – there are still all the elements of the genre in play here – but an examination of what makes men violent in a world seemingly ruined by bloodshed for decades. It’s just as these outlaws and dusty plain towns are on their way out that we see the plight of Will Munny, a man who knows very little outside of killing despite his best intentions. “Killing is a hell of a thing” he says, and Unforgiven is a beautiful, powerful examination into the blackest hearts of humanity.

Larry Taylor - Managing Editor
Larry Taylor - Managing Editor
Larry is the managing editor for Monkeys Fighting Robots. The Dalai Lama once told him when he dies he will receive total consciousness. So he's got that going for him... Which is nice.

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