The Clint Eastwood Directorial Retrospective – The 2000s

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The 2000s started pretty roughly for Eastwood, at least in terms of his directorial work. Opening the new century with Space Cowboys… admittedly not his best moment, but also not his worst. Space Cowboys has one hell of a cast, with Eastwood himself leading Tommy Lee Jones, Donald Sutherland and James Garner into space. It sounds like a joke, and there are plenty of moments of comedy relief in the film, but for the most part it is pretty serious, with Eastwood impressively managing to consistently toe the line between outright silliness, with Rocky-esque training montages featuring old men who can barely move, to moments of pure mortality, these heartbreaking displays of defeat at times when the men give up all hope, because of their age or otherwise. It’s a little too mixed-up for its own good, though, with the final act then adding in action and tension into a film that was only just managing to hold itself together trying to be funny and serious, and as sad as it is to admit it, it doesn’t work too well. It’s good fun, and entertaining, but it’s painfully by the books for the most part, the only thing that differentiates it as something from Eastwood is the frequently re-appearing theme of time passing and consciousness about age. Some of it is outright funny in a bad way, with some of the script just not working at all, which makes me wonder why Eastwood even took this script on in the first place as, usually, he’s better with his choosing, but I suppose we all win some and lose some. I can only really recommend this to the real enthusiasts, or people who want a silly space movie on a relaxed afternoon, but it is far from being worth seeking out for anybody, which is a real shame as there is… some potential here, it just isn’t utilised carefully enough.

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Following on from the pretty mediocre Space Cowboys, Eastwood made Blood Work, which is essentially the sixth Dirty Harry film – it’s safe to assume that Warner Bros stopped the Harry franchise because Eastwood was only getting older, but he proves here that he still had it in him to make a fun, popcorn crime thriller, and to do it pretty damn well. Clint is so good at being his typical grizzled cop that, to a certain extent, I’m glad he was typecast as one, I don’t think I could ever really grow tired of watching him grumble his way around whilst working for the greater good, and shockingly Jeff Daniels is also amazing here as Eastwood’s little sidekick. This one doesn’t really reveal all too much about Eastwood, with his previous few films feeling like a detraction from the work he was putting out in the early 1990s (Unforgiven, A Perfect World, The Bridges of Madison County) and going back to what he was doing in the 1980s, just making good little genre films and leaving it at that. This one is one of his most entertaining, but also one of his least fascinating. It’s mostly a pretty run-of-the-mill detective drama in terms of the plot, but thankfully the execution keeps it interesting and helps to keep an unassuming audience on their toes. 

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Finally returning to where he started, with documentary filmmaking, Eastwood made Piano Blues in 2003. Piano Blues was just one of seven films, made by a group of directors lead by Martin Scorsese on the Blues. Again, it is as if Eastwood got a little lazy or complacent here, as this one is mostly him talking to a few musicians and asking them to perform on camera, and archive footage during some of their conversations. It’s interesting to someone who doesn’t know much about the blues, and I can imagine that for fans of the blues this would be quite enjoyable, but it’s pretty bland documentary in terms of directing, with most of the fun coming from the conversation between Ray Charles and Eastwood, because Ray is so charismatic and Eastwood just seems pleased to be in the presence of such a man. Also interesting is that Eastwood reveals why he is so interested in the blues, explaining how when he was young it was all he would listen to after one day his mother came home with a few records. It’s vaguely amusing, but certainly not an Eastwood essential.

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But then, he came back and surprised us all once again. Mystic River, released the very same year as the Piano Blues documentary, is where you can see maybe the biggest change in Eastwood’s directorial work, this transformation into an incredibly precise, careful storyteller with a focus on realistic stories with pretty grim tones. He did a few of these in a row, but of course, we will get onto them later down the line. Mystic River is a brilliant film, receiving Eastwood Oscar nominations for both Best Picture and Best Directing, as well as Oscar wins for Sean Penn (Best Actor) and Tim Robbins (Best Supporting Actor). It’s no wonder that a film so technically well done managed to sweep the nominations, with an ensemble cast who all do some of their very best work here – even Kevin Bacon manages to do a fantastic job here as the detective stuck in the middle of the case, being connected to both the victim and the suspect since childhood – and many of the revelations that occur in the final act are just haunting, thanks to Brian Helgeland’s excellent script. The film is grim, it’s thrilling, it’s enticing and entertaining, and this was only really Eastwood’s first shot at something like this, with more to come that, for the most part, only seem to get better with every try, leading to much of his finest work. Mystic River was a huge change and it was phenomenally handled, giving both critics and audiences a whole new respect for Eastwood, maybe for the first time bringing the spotlight onto him as a director rather than a star as, for once, he isn’t actually in this film as he had been before with all of his most acclaimed and respected films. 

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The nominations for Best Director and Best Picture clearly weren’t satisfying enough for Eastwood though, as he quickly moved on and made Million Dollar Baby, perhaps his most famous and maybe his greatest work. Million Dollar Baby focuses on Maggie Fitzgerald, a female boxer desperate to be trained by Eastwood’s Frankie Dunn who, at first, outright refuses but eventually comes around. Featuring one of Eastwood’s best performances, his best directorial work and also one of the most touching scores… ever (also composed by Eastwood – evidently a man of many talents), as well as by far his most emotional storytelling, and maybe his saddest film of all, Million Dollar Baby’s stance on The American Dream is just incredible. Incredibly harsh, profoundly moving, and astonishingly well produced, earning Oscar wins for Eastwood for Best Picture and Best Director, as well as acting Oscars for Morgan Freeman, who plays the supporting trainer, Eddie “Scrap” Dupris and Swank for her portrayal of Fitzgerald. This is a film that I feel literally anybody can enjoy to a certain extent, it is both a moving drama, a provocatively vitriolic look at the American Dream (Fitzgerald is completely torn apart by it, in a way that can only be described as ruthless, and all of those who surround her are just as affected by it), all pushed along by some of the most impressive acting work I have ever seen, incredible direction and, as aforementioned, one of the most beautiful and emotive scores of recent memory. 

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Next is a real surprise, maybe the single boldest move of Eastwood’s entire career, the pairing of Flags of Our Fathers and Letters From Iwo Jima, both released in 2006. Flags of Our Fathers came first, and it is a film that focused on a small group of American soldiers (three servicemen) who were involved in the battle at Iwo Jima, looking mostly at the horror of the battle through a very Hollywoodised lens (think the sentimental parts of Saving Private Ryan, though not quite as bad) as well as the aftermath – the effects of the battle on the men involved. The most interesting point is how the men are changed by what they see, even if the delivery is a little questionable (I think this is the point, though). Before the battle, they are excited be involved in the fight for their country, and after it, when the media is glorifying their murderous actions, they all seem so distant. The direction is poignant, the performances are very good and the score is terrific, but this is one that I only really find interesting because of how it juxtaposes Letters From Iwo Jima.

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Speaking of Letters From Iwo Jima, it released just a few months after Flags of Our Fathers, and here’s the twist: It’s a 145 minute, black and white Japanese film that twists the plot of the last film, and now focuses on the Japanese battling to save Iwo Jima, their own land. With the bleakest tone of any film Eastwood has made – yes, including even Unforgiven, which focuses intently on a man whose past sins are so towering that he doesn’t even try to be a better man, he just gives in – the black and white, the long runtime and the slow pacing all give this one a completely different feel to the colourful, much quicker paced Flags. The contrast between the two is what really interests me. With a focus on the very same battle, from differing perspectives, I think it becomes clear that the two are set up to deny each other, one making the horror of the war from the American side quite poignant and the other making the sympathy for the Japanese unbearable. It’s one of his greatest films, incredibly strong formally and one of his most radical directing stylistic changes, going from something more sentimental than he typically would to his most savagely haunting film, and one that furthermore finds sympathy in the typical Eastwood villain – this is as revisionist as Eastwood ever got outside of his westerns (up to this point!), as it highlights his own troubles as a director in his focuses and completely flips his usual style for the sake of trying something new, and he makes it work wonders. It seems to me that almost every time he tries to really step in a new direction, it works, with very few exceptions. This one can’t be recommended enough, to anyone, especially if you can pair it with Flags of Our Fathers as it does make the experience all the more overwhelming due to the contrast between the two and knowing that they came from the same director, within the very same year, as they feel so incredibly different in style and focus despite the fact that their stories are so similar. 

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Two years later, another surprise – Changeling, starring Angelina Jolie as Christine Collins, depicting the true story of the hunt for a missing son and a great authoritarian injustice. Early on, Collins’ son goes missing, and her rampant hunt for him seems to do very little… until the police bring home a boy, saying it is her son. She says it isn’t, though, and it soon becomes clearer and clearer that they have brought her the wrong child. Of course, she goes to the police about this, and rather than investigate and continue searching for her child, they lock her in an asylum to rid of their problem. Eastwood’s angriest and most anti-authoritarian film since The Gauntlet (it easily surpasses that, too…), as well as his most clearly focused in terms of style in quite some time – everything here feels so precisely done, it’s really a wonder to watch. Jolie’s performance is great, but the meat of this film is certainly in the story itself which is totally riveting and utterly outrageous. Clint’s direction is slick, focused and calculated, maybe more so than ever… he’s just on top of his game here, and mostly is from here forwards. There’s little that can really be said for this film without ruining any of it, and doing that would be an awful thing to do, so go and see it!

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Also released in 2008 was Gran Torino, which may be the most famous film Eastwood directed, or at least the most popular one that is actually associated with him due to his starring role. Gran Torino follows a racist war veteran who slowly befriends his Asian-American neighbours, specifically the teenage boy Thao. With Eastwood’s typical hardass character, even exaggerated to the Nth degree here, this one is a little hard to look at as Eastwood wants us to. These stories of racial redemption are always tricky, and by focusing on the racist character rather than the victim of this racism it can become a little discomforting – I can only imagine how this film could have been if it was more from Thao’s perspective, rather than yet another white saviour kind of film, where Eastwood tries to help the neighbours deal with local gang warfare after seeing the trouble it causes. It’s an interesting film, specifically as Eastwood has frequently been in trouble in real life for his remarks surrounding race, and continues to use racial slurs in his films even now (The Mule features some pretty harsh dialogue, really), but it is difficult to view it as this great positive, progressive move as I think Eastwood really wants us to. Really, I find white saviour narratives incredibly tiring by this point, and there are so many of them already out there that this just feels quite pointless, almost disrespectful, even. 

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And ending the decade on a truly limp note, Invictus came out in 2009. This one really has very little special about it, telling the story of Nelson Mandela trying to help the issues with racial separation/apartheid through the rugby world cup. It’s a fine film, very much helped along by two terrific performances from Matt Damon and Morgan Freeman, but as I said, there’s little that is genuinely noteworthy about this one. It is Eastwood’s least energetic film, it just feels very stagnant for the most part, very safe and taking no risk. It’s a shame that he would end a decade of containing some of his best films with his least exciting one to date, however, I suppose it can’t be helped.

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Here is Clint directing Million Dollar Baby

That’s all for the 2000s, though! The final essay will be up soon, looking at his 7 films of the 2010s, which features some of his strangest films yet. Stay tuned!

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