Clint Eastwood: A Look Back at the Director’s Career

Clint EastwoodWell it appears that the 84 year old filmmaker does not show any signs of slowing down; his latest directorial effort is being released this weekend, Jersey Boys, and he already filmed his next project about the late great Seal sniper Chris Kyle, entitled American Sniper. So in honor of this weekend’s release, as well as, over forty years of directing movies, I thought it would be good to look back at Eastwood’s past efforts. So I would just like to remind the reader that this is my opinion; so here are my thoughts about Eastwood’s best, worst, most overrated, and best guilty pleasure films. 

Most Overrated 

Gran Torino (116 minutes, Rated R)

Gran Torino

Now, this one does hurt to say because I do like elements of Gran Torino; however, I have heard too many people say that this is Clint Eastwood’s best movie and that is the farthest thing from the truth. Is it the perfect role for Clint? Yes. Is it entertaining? Yes. But is it original or add anything to Eastwood’s storied career? No, in fact Gran Torino has not withstood the test of time; it feels dated for a movie that just came out six years ago.

And its biggest problem, which was my biggest criticism in 2008, is the kid actor. Was Bee Vang really the best choice for Thao; his acting is wooden and his line delivery is cringe-worthy. Perhaps, Vang’s performance suffered from Eastwood’s directorial style; Clint is notorious for only doing one-take and moving on. But to be honest, even with a million takes, I do not think the kid actor would have ever given a suitable performance: there is a reason why this was his first and only feature film credit.

But this all leads to the wonderfully predictable ending, which (SPOILER ALERT) has Walt sacrificing himself to save the neighborhood. The fact that he has the cough throughout indicates that he is a terminally ill man, which further telegraphs the inevitable conclusion. But his sacrifice would have been even greater, if he were perfectly healthy, which would have made it somewhat surprising as well.

And do not even get me started about the Jesus imagery, which is over emphasized by the over the top view; we get it, he is like Jesus because he saved everybody from the gang, but does it have to be that blatant. Again, I must remind people that I do not hate this movie; I remember in 2008 that I got choked up when he died. However, this is far from his best directorial effort and people need to realize that.

Guilty Pleasure

Heartbreak Ridge (130 minutes, Rated R)

Heartbreak Ridge, Clint Eastwood

While it should in no way be remembered as a so-called bad movie, it is nowhere near a good one either. Heartbreak Ridge follows a hard-nosed Marine gunnery Sergeant, Highway (Clint Eastwood), as he attempts to whip a platoon of spoiled recon soldiers into shape: he also consistently clashes with superiors (because we need conflict) and his ex-wife. Obviously, this is the atypical Eastwood character with a plot that has been seen a million times before. And it also does not help that Heartbreak Ridge does not age well; this was very much a product of the 80s.

However, I always found Heartbreak Ridge entertaining from beginning to end. The way it perfectly blended comedy and drama, shows a great director in the making; Ridge could be seen as stepping stone towards films like Million Dollar Baby, which worked perfectly as a ‘dramedy.’ At the same time, I realize that besides a select few in the platoon, particularly Mario Van Peebles’s Stitch, the rest of the cast are cardboard cutouts: characters that are so one dimensional that they have names like ‘Profile’ and ‘Swede.’

And the film stumbles to an ending that is anti-climactic and also feels like one giant infomercial for the Marines. But again, I always found this charming and even though I am aware of all these flaws, I always find myself watching Heartbreak Ridge when it is on cable.

Least Favorite

J. Edgar (137 minutes, Rated R)

J. Edgar, Clint Eastwood As a history major, who got really far with his degree, I was looking forward to J. Edgar. While I did not know how DiCaprio would fair in the role of Hoover, it was an interesting casting choice to say the least. What no one expected was how distracting the damn make up would be; I was so troubled throughout by it, that I kept wondering did they really test the make up before putting it in front of a camera? The Monty Python make up and effects from the 70s and 80s looked more realistic and they were playing it for laughs.

Now, most people focus their hate towards the prosthetics, which is warranted, but this horribly insipid movie drags along for almost two and a half hours. And I usually like sweeping historical biographies; DiCaprio’s turn as Howard Hughes in Scorsese’s The Aviator still remains one of my favorites. However, this long boring mess suffers from one huge problem, it is just not that interesting. This is something incredibly strange to say about a movie with an interesting character like Hoover: which just shows how bad Eastwood failed.

Mix this with a melodramatic sub-plot about Hoover’s alleged homosexuality and the fact that he is an extremely unlikable character, and the result is a bland picture that happens to be one of Eastwood’s worst. And trust me this was a hard selection because for as many directorial hits that he had, there were plenty of failures: Hereafter, The Rookie or the abundance of his 80s features.


Unforgiven (131 minutes, Rated R)

Unforgiven, Clint Eastwood

Commonly known as the post-Vietnam western, Unforgiven is Eastwood’s career summed up into one movie: and it also happens to be 1992s Best Picture Winner. While it was a hard task selecting a sole favorite, Million Dollar Baby, Mystic River and Letters of Iwo Jima were all viable, Unforgiven is the movie that established Eastwood’s directorial career. But this also distinguished him as an actor; he was no longer known as the scowling stereotype and showed that he can give a layered performance.

Furthermore, it also showed that he was capable of shooting a gorgeous landscape, as well as, nuanced violence; people died in grotesque ways, but it was not violence for the sake of it. Through everyone of Little Bill’s bullwhips or every gunshot fired, the viewer always felt the severity of the violence. Also, this was the first time that I saw Eastwood play a villain, yet somehow the viewer roots for his despicable character known as Bill Munny: who uttered these famous lines, “I’ve killed women and children. I’ve killed just about everything that walks or crawled at one time or another. And I’m here to kill you, Little Bill.”

Munny lacked a moral compass, yet for some reason his warped sense of justice connected with viewers. Not only did we root for Will Munny, but also, we wanted the only sense of authority, Little Bill (Gene Hackman), to die a horrible death; and while Little Bill is unlikable, he is still reasonably a good man.

This twisted look at the West takes the blinders off of a genre that glorified outlaws in the past; in a way, this pessimistic post-Vietnam western showed that everyday life is not ‘black and white.’ Eastwood’s character represents the grey area, which may not always be right, but could sometimes be justified. Needless to say, I can write hundreds of pages about Unforgiven, a picture that is as fun to talk about, as it is to watch.


And if you want to support my terrible habit of writing, please click on the Amazon links below to purchase other Eastwood films. If you do that, I receive a percentage of all transactions.

Amazon Buy: Clint Eastwood: 35 Film Collection

Amazon Buy: Heartbreak Ridge

Amazon Buy: Unforgiven [Blu-ray]

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