10 Best Movies Directed by Clint Eastwood (Of All Time)

Clint Eastwood

Welcome to our list setting out Clint Eastwood’s best movies he directed. Here we go…

10. Invictus (2009)

This film was under my radar until Matt Damon appeared  with an acting nomination at the Academy Awards. Damon has been on the fence for me as an actor. His best performances are always at the helm of a great director (think about it…) in the wrong hands, we all suffer. So after watching Damon’s emotional, inspiring, believable performance as rugby coach Francois Pienaar, I had to invest myself in the film and congratulate its director, Clint Eastwood. Not quite a biographical tale, not quite a sports film, Invictus takes its name from a William Ernet Henly poem, meaning, “unconquered.” And it delivers that thematic premise. It’s important to note Eastwood’s handling of theme in this directorial effort. The plot points are a tad predictable, but Eastwood is successful in pushing through to illustrate what it takes to drive a poverty-stricken nation to success. Inspiration is found on the playing field between two great leaders and their love for country.  The film is seamless in its editing, and intense on the playing field with its cinematography. Eastwood handles Morgan Freeman’s portrayal of Nelson Mandela well enough, although, its not one of Freeman’s best.

9. Absolute Power (1997)

Absolute Power firmly confirms Eastwood as a director who can not only handle the thriller genre, but also innovate it. From performance to script, lighting and sound the man knows how to layer suspense in a twisting and tense manner. Viewers are hooked from the end of the first sequence, which is arguably one of the best openings to a crime film ever, depicting what happens when a robber picks the wrong night to go to work. Most thrillers rely on cheap tricks, or fall flat halfway through the second act. Eastwood avoids this pitfall by offering us a relationship arc – an estranged father and daughter storyline (a Eastwood trademark). Few thrillers delve into personal stories, leaving the hero a simple action figure. But Eastwood uses this relationship to cohesively connect all the elements in the story. Thus, we know Luther Whitney as a person – flawed, determined, complicated. And alongside Joel Cox’s editing and Jack Green’s camera work, there are memorable “action sequences” with an no sound, dialogue, special effects, violence or cheap thrills – and they’re memorable simply because we are fully invested in the character and his story, alongside the plot. Absolute Power is a brilliant and rare feat.

8. The Bridges of Madison County (1995)

At first thought, one might say this is not your typical Eastwood film  – but it is precisely that. A film based on an idea, loss, regrets, simple gestures and controlled performances. This is an Eastwood classic – if you can handle him without the lasso, boots and cowboy hat. 
Eastwood plays a photographer, Robert Kincaid, and Meryl Streep plays farmer’s housewife, Francesca Johnson. The two meet, and what develops is a film about falling in love, and letting it go for the rest of your life. It’s heart-wrenchingly melancholic – and ever so powerful for that precise choice (thanks to author James Waller’s novel).  Two people who deserve one another, and the sad lesson, that life isn’t always just about what makes you happy. Only middle age lovers could conclude such a mature understanding and decide to carry that burden. The film is not erotic or sexy, it depicts love in the manner we wish to experience mind, body and soul. The two actors should be commended on their handling of character nuance. The landscape is captured magnificently by Jack Green’s cinematography, embossing candlelight with subtext. Soft diegetic sound (another Eastwood trademark) fills the silences that weight heavily on characters.

7. Bird (1988)

There is no doubt that Eastwood and his preferred musical tastes accent most of his directorial accomplishments. So if you happen to be a jazz fan, this film epitomizes his musical instincts. Bird is a musical biopic on the life of Charlie Parker, a 1940’s jazz legend who transformed the genre with his improvisational genius who ultimately succumbed to an early death due to his self-destructive habits.  Forrest Whitaker is phenomenal as Charlie Bird Parker, and delivers an acute and sympathetic performance under Eastwood’s guiding hand, alongside Diane Venora, in a strong portrayal of Chan Parker. Perhaps Eastwood’s own love of jazz allowed him the insight to capturing the dark mood, atmosphere and chaos of jazz clubs of the 40s and 50s in all aspects of bringing the story to life – light, camera, sound, and diction, and touchingly, the use of rain and soggy streets. Every element adds up in telling a story of a very inspirational and charming man who lead a damaged life. The film is well crafted, long and ambitious, but succeeds in its use of one artistic medium (film) to illustrate another (music).

6. Unforgiven (1992)

Eastwood was finally bestowed what he yearned for with this film at the 1993 Academy Awards – (his first) Best Director and Best Picture statuettes. However, to give the lone wolf of Westerns one of cinema’s highest honors for a Western…seems a little anticipated.  But, I must admit, in terms of Westerns, and performance, Unforgiven is a top act. To understand the appropriate execution of this film, one should look at its actor/director in terms of channeling the film’s point of view, and then the Oscar seems more than fitting. This film takes place in a time where the Old West is confronted with the New. An existence of simplicity and justice conflicted with greed and amorality, the righteous outlaws versus the cruel sheriff, or…the Eastwood of yester-year meets the new Eastwood of today.  The tone, visual style and soundscape of the film, reflect an era of storytelling long passed. But Eastwood manages to revitalize the long shot, master shot, backlit interiors, clipped dialogue, and themes of classic westerns in a modern and mindful manner. Eastwood is a master of detailing the inner working of a man filled with regret, sometimes in a not so shameful way. He delivers a story with authenticity and moral quandary – are all lives worth the same? To Eastwood’s William Munny – not in the slightest.

5. Flags Of Our Fathers (2006)

Perhaps it was all his time spent as the loner, but no working director today understands the individual quite like Clint. He is intelligent in drawing out a character, highlighting their aims, irks, passion and regrets.  Even more, is his ability as an American to maturely comment on his country, in the past and present.  Flags of our Fathers is a film based around the American soldiers who raised the U.S. flag atop Mt. Suribachi (Japan) on February 23, 1945. Eastwood’s film delves into the nameless solders in the photograph and their lives. Once again, Eastwood’s battle scenes are epic and quite effective in depicting the hell men on both fronts faced during the war.  Personally, I’ve never been a fan of Eastwood’s use of voiceover, and in none of his films that employed the device have I felt it was crucial to the story. However, in this film, the flow between the past and present, in uncovering the truth, and exploring a way of thinking, a love for your fellow man, and sometimes (but not always) country, Alongside its sister film, Letters from Iwo Jima, Eastwood masters the sentiments of each soldier and their identity versus the nations. A tough task, but Eastwood handles the matter with great instinct, ambition, and affection. The cinematography and silence found in the film dutifully capture the isolating and depressed landscape of war, of soldier, and one’s past.

4. Mystic River (2003)

Two distinct memories come to mind when I think about this film. One has to do with the very first time I saw it – which was in an absolute packed theatre, sitting in the very last row, mouth agape for the whole film. No lie – my jaw dropped from the first sequence until the last, which never happened to me watching a movie before. The second is the last time I watched it, which was only a few weeks ago in preparation for this review, and just like the first time I followed the mystery, sophistication and cool, and thought I knew what would happen, only to be surprised once again by the end. No lie  – the I placed faith in the plot twists that once again took me down the wrong path. Bravo! The film is worth a viewing for many reasons, and a second for almost a dozen more.  The story revolves around three childhood friends whose lives are forever changed after one of them, Dave Boyle (Tim Robbins) is abducted by a pedophile during a game of street hockey. Flash forward decades later, and the disconnected friends are almost unwillingly reunited after the death of Jimmy Markum’s (Sean Penn) eldest daughter, which spins this drama into a classic whodunit with Detective Sean Devine (Kevin Bacon) helming the investigation.  These three actors are superb in their parts, and a special kudos should go out to Marcia Gay Harden who plays Celeste, Dave’s puzzled wife. At first, her character is hard to swallow – but Harden brings a woman equally charged by her unfounded suspicions, family devotion, and fear to life in a quiet, unflattering powerhouse manner. A great casting choice Clint, and I’m not even a Harden fan. However the film’s unparalleled performance in this film belongs to Penn, a father racked by guilt, sorrow, revenge, and unconditional love. Clint’s handle on the characters and the actors hired to portray them is steady, authentic and quite poignant. This film unfolds as a sensitive revenge tale, which is often fuddled by the misgivings of a filmmaker, but not here. Clint, and writer Brian Helgeland keep true to Brian Lehane’s novel, where every character has tough choices to make and live by. Sympathies pour out for each of them, and suddenly vengeance is not so clearly cut from the cloth of right and wrong. The film’ setting is a blue-collared Boston neighborhood, and Clint’s visual aesthetic remains true to the raw, gritty, dagger cut lifestyle of your average Americans. Some of the eeriest scenes take place in the day, and it’s interesting to watch a man who mastered shadow and light, deliver the ominous under the sun. Once again Clint manages the score, which supports the characters’ mood and their stories. SEE this film if you haven’t, it will make you fall in love with cinema all over again.

3. Changeling (2008)

The only complaint I have for this film – is the trailer, which grossly misled the general public. Perhaps, in lieu of that marketing error, most people let Changeling slip by. Big mistake. This film is haunting. Absolutely spine-tingling. Clint Eastwood should be commended, alongside Angelina Jolie and John Malkovich. The film is based on a true story – and your jaw will drop through its viewings and numerous plot twists, turns, and revelations. It is impossible to not experience a range of emotions – anger, horror, sadness, empathy, and fear when viewing this film, and by its end you will feel nothing but gratitude, gratitude you are not Christine Collins. The film is about a missing Los Angeles child, circa 1928. Jolie plays the mother, Christine, who literally melts down with the inefficiency of the police department in locating her son, to near hysterics as they “find” her son, who Christine implores, is not her Walter.  For once, Jolie’s penchant for teary performances is well matched with the grace and cool of Mr. Malkovich’s Rev. Gustav Briegleb. There is not one bad performance in this piece, and Mr. Eastwood deserves kudos for the film’s many marvels. Nothing is done in excess. The cinematography renders an Old Hollywood feel with heavy blacks, blues and a myriad of other colours, essentially setting the right tone and mood for the dramatic thriller. Once again the score is done by the hands of Eastwood himself, and captures the somber, raw feel a mother undergoes in trying to find her son. You will not be disappointed.

2. The Outlaw Josey Wales (1976)

The Outlaw Josey Wales will change your opinion about Westerns for the rest of your life (if you haven’t seen it already). The story is about a bruised Missourian farmer turned guerrilla soldier, who refuses to surrender to peace or for amnesty, especially after the Civil war brutally claims his family and home.  It reminds me of the old adage, of the most dangerous people are the ones who have nothing lose. And as someone who holds a grudge, I can empathize with Wales’ needs to satisfy a most personal need following a code of honor unto himself. What marks this film from most Westerns, is its handling of the emotional palette.  Your feelings catapult from love, hate, sorrow, anger, etc following a character through a story dealing with very personal themes – revenge, forgiveness, solidarity (then the lack of it), death, racism, and betrayal. It’s a monstrous feat to touch upon either of these elements on their own, and here comes Clint bringing authenticity to them all.  Like a few of his greatest films, Clint opening sequence is apt and emotionally charged. Clint’s character doesn’t speak much, but that is the Classic Cowboy, and what dialogue persists in the film are memorable (“dying ain’t no way to make a living”) and pertinent. But watch his face! Watch the expressions – he knows what audiences needs to see and hear in a character, and he delivers. Great instincts for such a character, and great instincts in the supporting cast, especially by Chief Dan George (Lone Waitie) and Clint’s one-time real life love, Sondra Locke as Laura Lee. What a Western relishes on is character complexity under the guise of simplicity or stock character. Wales’ truest motivations and intentions kept, and so his take on humanity is something we can’t judge. Every plot point is progressed by consequences rendered by decisions, and the “cause and effect” method suits the story almost perfectly.  Morally relevant, especially in today’s climate, the film deals with the winners and losers of war, in a truly captivating effort, with an ending that rivals the best of them. You will wish there was a sequel – and that’s rarely uttered by cinephiles.

(Final Note: I tossed and turned in feeling it should be in the number one spot)

1. Million Dollar Baby (2004)

Sometimes you watch a film and can note a trademark or two of the director, a clever or preferred story device, editing trick, or catchphrase that time and again appears in their subsequent works. But when you watch Million Dollar Baby you are experiencing a director’s storytelling philosophy come to life from the first frame to the last. This is Eastwood’s masterpiece plain and simple. Every element he values as a filmmaker is at its top form in this film. The film is edgy, charged, and emotionally devastating and at its end there is nothing short but the quintessential catharsis that the Greeks wrote and died for. The boxing ring acts as a metaphor for life, and is explained as so by the film’s narrator “Scrap Iron” Dupris (Freeman). He channels the story of an aged fight trainer, Frank (Eastwood) and the trailer-park underdog, Maggie (Swank) who wishes to be the next champ. Thematically, the film covers Eastwood’s favorites – nobility, regret, honour, corruption and friendship. Every actor commands the screen, and no one can deny that Swank exists on screen as Maggie, complete and total immersion into her role. Each character battles their demons, and faces the consequences in a perfectly structured screenplay, based on F.X. Toole’s short stories. Not since The Godfather do I remember a film that is so dimly light that shadows sometimes say more than characters themselves. The fights are choreographed and piercing. The score is almost regal; a soft requiem for all that is lost.  This film captures your absolute attention and every character has a place in your mind and heart. It is nothing short of real.

– Jennifer Kassabian

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