The Clint Eastwood Directorial Retrospective – The 1990s

The 1990s were a very interesting time for Eastwood’s work, giving maybe his most diverse collection of films. We got a film based on the behind-the-scenes antics on John Huston’s The African Queen, a buddy cop movie where Eastwood gives way to the next generation… and then doesn’t, a romance, a voodoo crime courtroom comedy (yes, really!) and Eastwood’s last western.

As with 1980, Eastwood opened the decade with some efficiency, releasing two films he directed and starred in 1990. The first of these two was White Hunter, Black Heart – a film vaguely based on the story of John Huston elephant hunting behind the scenes of The African Queen, with Eastwood playing Huston. In the film, the focus is much more on one obsession detracting from another. It’s one of Eastwood’s most abstract, most difficult to really get into, at times being genuinely quite alienating with the focus on a man driven to obsession by hunting elephants, however, there is something within the framing that makes it work nonetheless. There is this creeping mania to it, something that gradually emerges and shows itself more and more as the runtime goes along until it becomes unavoidable. Just seeing Eastwood transform, too, in both his form behind the camera and his performance as John Wilson (they didn’t name him directly after Huston, likely to avoid a lawsuit as this isn’t too positive of a representation) is what is really memorable about this. It’s as if he, too, grew obsessed with what he was doing whilst in Africa filming, and you can see something in him here that you don’t see anywhere else, which makes it well worth seeing. Seeing Eastwood go from his typical representation of an artist as someone who is a little destructive, but always gets the job done (hell, this applies to his cop characters, too – they often do some… questionable things that pay off in the end when they catch the villain) to this man driven insane turning into a monster in front of us is insane, something we would never really see again in him.

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Of course, he couldn’t keep presenting himself that way forever, and he didn’t waste time in going back to how things where with The Rookie, which released the same year. A buddy cop film starring Charlie Sheen as the titular Rookie and Eastwood as his superior, the film is just full of exciting set-pieces and jokes – it’s a great time, until suddenly… it’s not anymore. The first hour or so is very relaxed, it’s full of those fish-out-of-water first day on the job jokes that are charming, and every set-piece is great fun (you can tell that maybe let Eastwood have a little too much money, and that he squeezed every cent out of the budget just so he could have some cars flipping over constantly), until all of a sudden, Eastwood’s character is kidnapped, and Sheen takes up the screen in his mission to save Clint. From there, it goes completely off the rails in the most baffling but wonderful way. It shows that Eastwood didn’t really know how to handle all of these ideas in one film, and so you end up with Sheen turning into one of the most disgusting ideals of a police officer I have EVER seen put to screen, walking into a bar, attacking those inside and torching the place in a genuinely alarming momentary rampage, brought on not by the people in the bar (they don’t help the situation, but it’s definitely not their fault either) but by Sheen’s character’s own guilt over the death of his brother from childhood. Then add on the bizarre moment where one of the women who kidnapped Eastwood essentially rapes him whilst he is tied up (not helped by the fact that Sheen’s character makes a few passing jokes about it when he arrives, though at least Eastwood does react with hostility then), and you have some of the strangest stuff he has ever done. It’s complete chaos, almost impossible to really pin down as Eastwood never frames anything in a specific way morally, he just keeps everything the same and so, you can never really tell if he’s making a joke or glorifying something or not. Add onto all of that insanity the fact that his style also went completely insane as the film goes on, opening with a bizarre dream sequence before calming down again right up until that second half switch, before all becomes insane once again  and the cinematography really makes everything so much more uncomfortable, with dizzying fish-eye close-ups and aerial motorcycle shots that tilt from side to side. It’s also just quite nice to see Lara Flynn Boyle in a film, too.

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Now for quite the switch, heading into a new era for Eastwood where he was completely unafraid of wearing his heart on his sleeve. Unforgiven came out in 1992, and follows the story of William Munny, a widower looking after his children and his hogs, hiding from the past… that is until he is approached by The Schofield Kid with an opportunity to make enough money to give his children a good life for killing two cowboys who cut up a prostitute in the town of Big Whiskey. Munny re-unites with his old partner, Ned (played brilliantly by Morgan Freeman) and heads to Big Whiskey, but things aren’t quite as they seem, with the questionable Sheriff Little Bill (played by Gene Hackman, in one of his best performances). There’s good reason that this is Eastwood’s most recognisable and most acclaimed film – it’s a masterpiece, and definitely his bleakest film up to the time when he released it (arguably, it hasn’t been topped, either). It’s also surprisingly nuanced, with huge changes happening completely unannounced, such as a certain scene towards the end involving alcohol. What really makes the film so impressive for me, though, is the look at some things being completely unforgivable. With the mentions of Munny’s past actions mostly being quite brief, such as him bringing up shooting a man, making his teeth coming out the back of his head and his troubles with women and children, and in the final act, Munny genuinely becomes frightening, nightmarish, despite the reasoning behind his actions. He is the most intimidating western character right alongside Liberty Valance, and the kind of character you never really look at the same way once seeing them in their darkest moment. A phenomenal film, really, and one of the very best films in a career full of wonders.

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The year after, A Perfect World came out, another surprisingly tender film coming from the typically grizzled Eastwood. Focusing on Kevin Costner as a recent prison escapee, who then kidnaps a young boy whilst on the run, the two form a close friendship (more of a father/son bond, similarly to The Rookie with its focus on generational friendship). Eastwood plays the cop hot on Costner’s tail, and, to the surprise of many, it’s actually a very pleasant and wholesome film. A road trip film with plenty of goofy antics on the part of the police characters and so many beautiful moments coming from both the landscapes shown and the activities that Costner’s charming jailbird and his new accomplice get up to, including stealing a Casper the Friendly Ghost costume before getting shot at by the police, but what is really surprisingly is how hard the ending hits. Of course, the fun and games must eventually come to an end, and they definitely do here, but even during these moments of turmoil at the end, the film doesn’t drop the wholesome charm in favour for the sadness, instead carrying both at the same time creating this stunning bittersweet tinge that can then be applied to the entirety of the film in retrospect. It’s one of Eastwood’s most surprising films in many ways, stunning in its emotional versatility, and as proof of Eastwood’s own cinematic/directorial versatility, too.

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Following one surprise with an even bigger one, in typical Eastwood fashion, The Bridges of Madison County came out in 1995, two years after A Perfect World. Eastwood’s most surprising film (other than Hereafter – more on that later), a romance starring himself alongside Meryl Streep. Eastwood plays photographer Robert Kincaid, who befriends and has a brief romance with Streep’s Francesca Johnson for four days during the 1960s. Using the death of Streep’s character in present day, and her children stumbling across her diary, as the way to tell the story adds to the bittersweet feeling that comes with knowing that this romance existed but never really came into fruition as it should have, with Eastwood’s recognisable trait of looking at time through a damning, melancholic lens, his fear of time passing once again projected onto the screen through his characters and their actions. Interestingly, the film also has a certain focus on dirty laundry, with one of the main reasons for their romance being as restricted as it is the fear of the opinions of others (Eastwood once again reflecting All That Heaven Allows, similarly to how he did in Breezy twenty years before), with one scene showing the scorn received by one woman who was caught having an affair. It’s fascinating that Eastwood shows such an insight into the romance here, just as it is baffling that he seems to show such a strong understanding of what makes the genre really work – he seems to get the balance between tension and love perfect here, something I can’t say for many films at all – and just knowing that Eastwood is sitting behind the camera will probably always be baffling. This one may be his absolute best film, surprise or not. It’s an incredible romance, one of the most bittersweet films of the 1990s and features two of the best performances from two of the greatest actors of all time. What’s not to love?

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Bringing in yet another incredible switch, and further proof of his incredibly versatility, Eastwood’s next film was a political crime thriller, Absolute Power, one of his most surprising films (again…). Opening with one of the most agonisingly slow opening acts to come from mainstream Hollywood, and one of the most sadistic and bizarre inciting incidents (not the incident itself, but the way it is presented in this incredibly uncomfortable set piece that seems to go on for way too long in the most brilliant way) and only getting stranger, this is the first time – for me, anyway – that Eastwood’s influences became so clear, with De Palma and Hitchcock being splattered all over this one and it being a surprisingly large jump from his other work, especially from his most recent output which had been much more tender towards his characters. Seeing that sudden contrast, especially from A Perfect World and The Bridges of Madison County, that drastic change from beautiful bittersweet films about relationships to this vitriolic, bitter, angry film about corruption in the government, is fascinating. Honestly, during the 1990s any radical change in genre and/or style from Eastwood became unsurprising towards the end, with him completely changing his genre, and then completely changing his form and style to fit whatever genre he was working with at the time, creating a group of fascinating films to look into in detail as they all reveal so much about how he works, and also show his endless ambition to always do more than he has been. Absolute Power is one of his most overlooked films, with the majority of Eastwood fans even skipping it (understandably… I admit even I needed a push to watch this one), but it is one of the most rewarding of all of his films, and one of the ones most worth viewing, both for those interested in cinema in general and those who are specifically looking into Eastwood’s work. 

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The very same year, Eastwood dropped another of his strangest films in his adaptation of Midnight in the Garden of Good and Evil. It’s a struggle to describe the plot, never mind the strange form that is used to tell the story, but I’ll just say that the film is about a reporter (John Cusack) who goes to a party started by a rich millionaire (Kevin Spacey), and when someone is murdered at the end of the night, Spacey is presumed guilty, and the rest of the film follows Cusack and the rest of the town as they try to figure out who the murderer is, whether they try to find out through detective work or… literal voodoo… yeah, I don’t know either. What makes this film even stranger is the tone, which bounces between the serious implications of the crime at the centre of the mystery to jokes about the characters, mostly pointed at the ‘weird’ ones who are easier to mock. The form is mostly very cold, too, which doesn’t help considering how strange and off the rails the story becomes (and the speed at which this happens is stunning, too). I’ve never been so bored and yet so intrigued by a film at the same time, with the story being predictable in many ways but completely unpredictable in the representations of characters and the way that the story moves, it’s the outcomes and the ending that are predictable (from the opening shot, one is pretty much able to predict everything that’ll happen by the end, so long as they’ve read the plot synopsis, anyway), making this weird phenomena where you know exactly what’s going to happen for the entire 150 minute runtime, and are just waiting for the reveal, and surely enough, you’re right the entire time. This one just didn’t do anything for me, and it does seem be one of Eastwood’s most divisive films, both amongst his fans and just in general. I do recommend giving it a shot, especially if it sounds interesting to you – there’s good chance that a lot of you could take something out of it and enjoy it quite a bit. 

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The final film of Eastwood’s 1990s was True Crime, admittedly one of his less interesting projects, but still a good one. This time, Eastwood stars as an alcoholic deadbeat reporter who suddenly realises that a man on death row, set to be killed tonight, is in fact innocent, with the film detailing his race against time to find the evidence and save the prisoner, Frank Beechum. For the most part, this one is pretty predictable, but it’s still interesting, and definitely entertaining. Some scenes really hit too, especially those focused on Beechum in prison when he is visited by his family, seeing them all trying to hold it together in what they believe is the final hours of his life, all based around a crime that we know he didn’t commit. It’s also interesting to me that Eastwood once again went back to his anti-authority ideologies just two years after Absolute Power. This one definitely isn’t as vitriolic as Absolute Power, but that doesn’t mean that it’s powerless, this one is careful about inferring that authorities are simply too lazy to look into crime properly, and base their arrests on intuition much more than they should, potentially even suggesting racial prejudice. It’s a surface level film, specifically in the form, but the ideas behind it are interesting. Worthwhile for any Eastwood enthusiast.

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So, that now concludes the 1990s, what is your favourite film from this decade from Eastwood? I’ll be back soon with the fourth part to this retrospective, which will focus on the 2000s, which is another huge change!

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