Clint Eastwood The Director: The 2000s

Eastwood’s first two films of the 2000s were genre exercises – but ones that acknowledge his age more than most of his previous work did. In 2000 he made Space Cowboys, co-starring Tommy Lee Jones, Donald Sutherland and James Garner who along with Eastwood himself played former astronauts who, for reasons too complicated to explain, are re-enlisted to head back to space. If you accept the concept, than Space Cowboys is a lot of fun. Interestingly, Eastwood gives Jones the best role instead of himself. It’s great to see these four play off each other, even if the film is basically an act of nostalgia.

2002’s Blood Work has Eastwood as a former FBI agent, recovering from a heart transplant, who returns to work to catch a serial killer. Like Absolute Power, no one going to claim that Blood Work is a great film – but as a thriller, the film works remarkably well – with Eastwood once again playing off his own image as a tough guy, and complicating it a little. It’s better than it really has any right to be.

2003 marked a definite change for Eastwood. With 23 films as a director – in which he starred in all but three (Breezy, Bird and Midnight in the Garden of Good and Evil), Eastwood started to move away from himself as the star. Over his next 10 films (including Jersey Boys) he would only star in two of them – rightly sensing, I think, there was only so much he could do as a director if he was saddled with a man over 70 as his star.

2003’s Mystic River is one of Eastwood’s very best films. It stars Sean Penn, Kevin Bacon and Tim Robbins as three childhood friends, who have forever been shaped by an event in their childhood – where one of them was kidnapped by a pedophile, and the other two got away. Now, decades later, Sean Penn – a family man whose dealings are not exactly all legal – has had his daughter kidnapped and murdered. Bacon plays the cop trying to solve the case, and Robbins, as the man who was kidnapped, is one of the lead suspects. Mystic River is about the causes and effects of violence – how what happens in childhood can haunt you forever. The three lead performances are all great – Penn and Robbins both won Oscars, and Bacon is just as good as they are (although in a far subtler performance, which is probably why he didn’t get much awards love). Marcia Gay Harden, as Robbins’ wife who suspects her husband is guilty, and Laura Linney as Penn’s wife are both excellent (Linney only has one great scene – but it’s a doozy). While Eastwood has a reputation for making violent films, more often than not, he questions that violence – and what it all means. In Mystic River, he has made one of his best films on the subject – and one of the very best films of his career as a director.

2004’s Million Dollar Baby was the second film for which Eastwood would win Oscars for Directing and Producing,

as well as the second time he would be nominated for a Best Actor Oscar. The film came out of nowhere in the Oscar race in 2004, releasing very late in the year, but proved to be one of the best – and certainly most emotional – films of Eastwood’s career. In it, he plays an aging boxing trainer – working at a rundown club, alongside his friend (played by Morgan Freeman). A young woman (Hilary Swank) shows up and wants to train with him – but he doesn’t train girls. Eventually, she wins him over – and he helps her become a great boxer, until tragedy strikes. The film is acting showcase for its three leads – like Mystic River, it won two acting Oscars -  Morgan Freeman and Hilary Swank – but I think it’s Eastwood’s performance which is the best in the movie. Once again, he plays a stubborn man who plays by his own rules – but it’s a great performance, and one that as the film winds down packs an emotional wallop. The film really does sneak up on you – and is one of Eastwood’s best.

To follow-up his Oscar winning film, Eastwood embarked on dual projects that may just be the most ambitious of his career. In 2006, he released two films, three months apart – Flags of Our Fathers and Letter from Iwo Jima – both of which looked at the WWII battle on the Japanese island of Iwo Jima – one from the American side, and one from the Japanese. Flags of Our Fathers came first – and is the more ambitious, but also more flawed of the two films. Eastwood’s film follows the men who raised the American flag on Iwo Jima that produced one of the most iconic photographs of the 20^th Century – before, during and after the battle. This is a more complex look at the idea of heroism than we normally get in WWII movies (more so than say John Wayne’s Sands of Iwo Jima for example), and how these men are used after that photo to sell war bonds. All the flash forwards and flash backs make the film a little complicated and messy at times, but this is still an excellent film. Letters from Iwo Jima is an even better film – daring not so much in it structure – it’s a little more straight forward than Flags – but because it’s one of the only American films to portray the Japanese in WWII in a sympathetic light. Watching

the films together definitely makes them both better than they are alone and adds up to a dual portrait of men who are willing to fight – and die – for their country – no matter what country that may be.

To me, Flags and Letters are the last two great films Eastwood has made – at least so far. He has directed five films between them and Jersey Boys – and while I think one is perhaps the worst film he has ever made, the other four are least good – even if they never quite rise to his best work.

In 2008, he made Changeling – starring Angelina Jolie as a mother in 1920s Los Angeles

whose child goes missing, and when he is found, she insists that the child they give her is not the one she lost. The period detail is excellent; Angelina Jolie is given a great, although somewhat one note role that she is nevertheless very good in. The best performance though is by Jason Butler Hamer, as a serial killer of young boys who is truly terrifying. Somewhat like Midnight in the Garden of Good and Evil, the film is perhaps too ambitious – a little too sprawling for a director like Eastwood, who is used to more focused material. It’s a good film, but in different hands, I wonder if it couldn’t have been great.

Later that same year Eastwood made his final screen appearance in one of his own films

(and second last overall) in Gran Torino. The movie is a little bit of a mess – with not very good performances by the entire supporting cast. The plot, about an Asian gang trying to recruit a neighbor of Eastwood’s, is also a little sloppy. Yet, it is worth seeing because Eastwood is great in the lead role – a gruff, racist old timer with a shotgun who growls “Get off my lawn”. The view of gang life and race relations is simplistic in the extreme – but I didn’t much care, since Eastwood is so good in the title role. He is playing with his iconic image more than ever before – playing it for laughs early on, and then deepening it. We think we know how it’s going to end – but we’re wrong. To me, it’s almost a shame Eastwood starred in the decent Trouble with the Curve (2012) after making this film – as the final image of him in this film, would have been the perfect one to end his directing career on – one that is far different from what we expect from him, but still somewhat fitting.

Eastwood was back it again the next year with Invictus – in which he direct Morgan Freeman as Nelson Mandela, who in the days after he is elected President, does the unexpected and embraces the all-white South African rugby team as they prepare for the World Cup to be played on their soil. Mandela is tired of the divisions in his country, and wants to bring everyone together. As a showcase for Morgan Freeman – who landed another Oscar nomination for the role – the film works just fine. The rest is typical, boilerplate inspirational sports movie stuff (how Matt Damon, as the Captain of the rugby team got an Oscar nomination, I’ll never know). The film is effective, but never great.

2010’s Hereafter is undoubtedly my least favorite Eastwood film ever. It’s a confused mess

of a film, with an impressive tsunami special effects sequence at the beginning of the film, and then tries to weave three stories together – that of a psychic (Matt Damon) twin boys, and a woman obsessed with life after death (Cecile de French). Watching the film, I kept expecting it to come together in some way, shape or form – we know that the three stories, which seem isolated, will come crashing together – and when they finally do, it’s a letdown. The film isn’t so much ambiguous as it is confused – and by the end, I was simply bored. I’m not sure what Clint was trying to say in the movie – but I don’t think he managed it.

Eastwood’s final, pre-Jersey Boys project, was 2011’s J. Edgar – which was mostly greeted

with yawns when it came out, but that I actually think is his best since the dual films of Flags and Letters. Leonardo DiCaprio may not be my first choice to play J. Edgar Hoover, but I think he does a great job playing the paranoid head of the FBI, who denied himself what he truly wanted for his entire life. The movie spans decades in his life, and remains ambiguous as to what exactly his relationship with the Armie Hamer character is – but we know that at the very least, Hoover is in love with him. Perhaps Eastwood does try to cram too much in – from Hoover’s days chasing bank robbers to the Lindbergh kidnapping to his conflict with the Kennedys to Nixon’s ambition – but as an old school biopic, I found the film fascinating – with a great performance by DiCaprio, and another great one by Judi Dench (her line reading of “I would rather have a dead son than a daffodil for a son” is chilling). It’s not quite Eastwood’s best work – but I do think it was criminally underrated in 2011.

That brings us up to date on the career of Clint Eastwood – the director. This weekend sees the release of Jersey Boys – a musical based on the hit stage play, and something I never would have picked as a Clint Eastwood film. The reviews have largely been mixed so far – so I doubt we’re looking at another Clint masterpiece. But even though the man in his mid-80s now, I have doubt that he is still capable of producing one. He’s already at work on his next film – American Sniper – a project Steven Spielberg pulled out of.

Eastwood is one of the most interesting American filmmakers in history. He didn’t start directing until he was 41 years old – an age in which many directors have already made their best films. Eastwood’s best film was made when he was 62 – Unforgiven – and many of his most interesting films came after he turned 70. Eventually, of course, time will catch up to him- he does turn 84 this year. But I hope we get a few more films from Eastwood. It may be a while since he made his last great film – but he’s capable of making another one.