Top Ten Clint Eastwood Directorial Achievements (part 2)

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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

#10 – 6 (Click here)

  1. David says


    What a pleasant surprise to read such insightful analysis of Mr Eastwood’s work! I have no complaint with your list except that reading it I’m reminded of another half dozen Eastwood films that could equally be included &, yes, I do think the great Gran Torino should have been on there. :-)

    But as for number one I totally agree with you on Million Dollar Baby. It’s a brilliant film, so delicately exquisite in its emotions & the way it ultimately ends up as a testament to how loving a father the Eastwood character really is, is staggering. You just hope that his daughter reads Scrap’s letter. Incidentally on the subject of voiceovers I think the use of it in M$B is amazing. That final line of Freeman’s where it becomes clear to the audience that his narration is actually him reading the letter he’s written to Frankie’s daughter – that in effect the entire film is being told as something that happened in the past – was simply stunning. It’s a profoundly stirring film, Million Dollar Baby. There’s something about it that stirs the soul.

    Re Flags of Our Fathers – great to read praise for this as I think its view of war as a multiplicity of perspectives is not only deeply insightful but thoughtful & fascinating viewing. That scene when one of the sailors falls into the water & the joking from those onboard slowly subsides when they realize the fleet can’t stop to pick him up has stayed with me as a metaphor for the plight of the flag-raisers in that film. Like that poor sailor their country moved on once the war ended but somehow the men who were briefly the center of attention got left behind.

    As for The Outlaw Josey Wales the thing I love is that it works on two levels; as a great action-revenge movie with lots of humour, & as a story about the healing of a brutalised man. Josey goes from family man to ruthless killer who just wants to be left alone. But the stragglers he attracts form a surrogate family & in their way they re-civilize him. They make him aware once again of the possibility of rejoining civilisation. The question is can he do it even if he wanted to?

    There’s so much to say about Eastwood & his wonderful movies. I think he’s a truly great artist.

  2. Jacob Barker says

    What can I say? I don ‘t like Million Dollar Baby! I’ve seen it twice and both times I felt like sitting through it was chore. I have absolutely no complaint about the picture it just didn’t speak to me!
    Mystic River – Great, depressing but great! How many times have you come home from work and said to yourself ‘I think I’m going to throw on Mystic River”!
    Changeling – Great!
    The Outlaw Josey Wales – Great!

    I also did prefer Letters from Iwo Jima much more than Flags!

    And Unforgiven would be my number one but your list does make me want to go back and re-watch some of his older films!

    Well Done Jen!

  3. Dave Valentine says

    Nice list but I am inclined to agree with a couple of Phil’s points. Mostly the absence of the masterful High Plains Drifter, which succesfully crosses the horror and Western genres with a very welcome twist of the surreal. Unforgiven ought to be higher, really.

    However, Million Dollar Baby is a staggering piece of work. That closing act hit me like one of Mo Chuisle’s powerful punches! Incredible film and a well deserved Oscar for Eastwood’s directing.

    Glad to see that the vastly over-praised Gran Torino didn’t feature. I found it to be lightly enjoyable but ultimately a big let down.

    The inclusion of The Changeling in second place has only spurred my need to see it even more urgent!

    Nice work Jen.

    1. Ricky says


      Seriously it is nice to see a list that did not only include his westerns!

      Good job!

  4. jen says

    Fair enough Phil, I can see where you’re coming from…. those are great westerns as well, and there was a moment I was seduced to solely discuss his work on the Western genre. However…I felt that was too minute of a discussion on such a great director. Play Misty for Me, personally, comes second to what better films managed to achieve in terms of mood, locale, montage and emotional response, I think of Vertigo, Psycho, and even Fatal Attraction…and High Plains Drifter, yes, is a great film, and I know Westerns play on the archetype enough times…I just thought Eastwoods work in this one…a little over stressed and less stylized. But yes, its a good film. I know Unforgiven is a lot of people’s favorite…however in terms of Westerns..I stand behind TOJW. Tell you what, I’ll try and revisit LTIJ just for you! peace.

  5. Phil says

    This list is so wrong in so many ways. First you omitted two of his best films – Play Misty For Me and High Plains Drifter which also happen to be two of the best westerns of all time and defiantly on my all time greatest American movies list. Also where the hell is Pale Rider? With the movies you did choose, Unforgiven should definitely be in the number one spot and why would you choose Flags of
    Our Fathers over Letters to Iwo Jima? Flags is formulaic, dull and Letters is groundbreaking, challenging and nearly flawless.

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