The FULL Clint Eastwood Retrospective (and ranking)

The work of Clint Eastwood is… hard to pin down to say the very least. Trying to effectively figure out the man behind the camera throughout the majority of his almost 5 decade long career proved much more difficult than one may expect, with me being one of many who seem to just assume he’s always just as grizzled and moody as he is in his performances. By looking more into his directorial work, another side – or even multiple new sides – open up, revealing one of the most interesting filmographies in memory. This sprawling, baffling filmography shows real growth throughout, with so many small changes and tweaks in terms of both ideology discussed and the form itself that it’s hard to believe. Going through was… quite an adventure, and so I figure I’ll discuss my experiences and thoughts on going through his body of work, looking at how his work evolved and grew over time. The only one I was unable to find was his debut documentary behind the scenes of The Beguiled (Don Siegel, 1971), so I like to think that I investigated plenty. I may also include some brief points at films he starred in, as this is intended to be an overall study of Eastwood as a film icon, so it makes sense to touch slightly on additional Malpaso productions throughout!

So, Eastwood’s breakthrough came in the infamous Man With No Name trilogy – a series of three spaghetti westerns directed by Sergio Leone, released in 1964, ’65 and ’66. His performance as the man with no name, a mysterious badass with the aim of a God who wandered from town to town, clearing them of anyone who gets in the way before moving on gave Eastwood an almost instant fame, with him being recognised as perhaps the biggest western star alongside John Wayne from the off. 

With Eastwood being a man who never quite seems completely satisfied with his achievements, it wasn’t much of a surprise to find out that – whilst his acting career continued to grow and blossom, building him into one of the most recognisable stars to ever touch the big screen – he soon turned to directing and (often) producing his own films. This started with a short behind-the-scenes documentary surrounding The Beguiled, a film directed by Don Siegel that Eastwood starred in, that was made and ‘released’ (one print is known to exist now, and that one print has been shown very few times) in 1971. In the same year, Eastwood released his own feature, Play Misty For Me.
Play Misty for Me is a thriller about a radio DJ (played by Eastwood himself) who finds himself in trouble when a huge fan starts stalking and harassing him. It starts off innocently, a budding romance between Eastwood and the manic fan, played by Jessica Walter. Coming out only a few years after Eastwood became popular, and during what may just be the peak of his popularity in the early 1970s (with the release of Dirty Harry – a film that Play Misty for Me makes a small cameo in early on), it’s hard to ignore the paranoia on show here about the relationship between celebrity and fan being so messy. Despite the fact that Eastwood had been married for almost twenty years when he made Play Misty for Me, there is a thick tension given to the feeling that comes from trying to associate yourself with someone who knows you more than you know them, it is maybe that idea that Eastwood fears the most here. What starts as a brief fling soon turns into a freakish nightmare, think Fatal Attraction, and the focus is much more about how Eastwood’s character reacts to this as opposed to the action itself, which is fascinating. The paranoia is brought to the foreground, changes in how Eastwood himself acts become noticeable and these changes in character become markings of a man who feels trapped by his own celebrity rather than gifted by it. It makes a lot of sense coming from someone who was as  popular as Eastwood was during the early 1970s, and the context surrounding the film only serves to make it all the more interesting and powerful.

Two years later, in 1973, Eastwood returned to the director’s chair with High Plains Drifter, a western focusing on a new cowboy in town who is asked to fend off some outlaws who are on the way. Bringing to mind the late work of John Ford in a way that no director ever really has, Eastwood brings the revisionist western traits to the forefront and forces his audience to focus on them. One scene in particular looks as a traumatising event experiences by Eastwood’s gunfighter, with his performance, the grim chiaroscuro lighting and the dizzying cinematography used in the moment to make the scene uncomfortable in a way that Eastwood never had before, really humanising his nameless ‘stranger’ through his experiences. It’s one of the best moments of his entire career, and the film itself could easily be placed in his ten best efforts. It’s one of the best westerns of the 1970s, even if Eastwood later did even better.

Making another huge leap in genre, from thriller to western and now into romance, Breezy came out. Released in the same year as High Plains Drifter, the film really proves Eastwood’s cinematic versatility. As similar as many of his performances are (although you can argue that he worked to disprove his typecast acting in the most vulnerable parts of High Plains Drifter, and also by making the small jump from cowboy to cop with the Dirty Harry series, which received it’s second film in 1973 with The Enforcer), it’s hard to deny his versatility from behind the camera, something that still surprises his audience even now. Breezy can most easily be explained as beautiful. The film focuses on a lonely, middle aged Frank Holden (played wonderfully by William Holden), a man who seems to have given up on love after a divorce who meets Breezy, a ‘teen-aged hippy with a big heart’. With a similar focus to Ali: Fear Eats The Soul (Rainer Werner Fassbinder, 1974), Breezy looks into the stigma surrounding age difference in relationships, both internal and external. Many scenes clearly point out the scorn that comes from others, but just as many look into the more internal paranoia that comes from the worrying about what others may think. It’s a tough film to get through at times, often due to the paranoia being so strong that the audience is forced into feeling a similar way to the characters, however, Breezy herself has such a charm that it is easy to overlook some of the pain shown and is played so brilliantly by Kay Lenz, who (fun fact) was asked to play Annie Hall later on, but refused as her husband didn’t want her to be involved. It’s also the film that maybe shows Eastwood’s influences most clearly, with many mirror shots bringing to mind the work of Douglas Sirk, matched with the chiaroscuro lighting style of Nicholas Ray’s Bigger than Life, tipping the hat in a way that Eastwood never really had before… and never really would again.
One more thing of note surrounding Breezy is the way that it looks at the romance shared between the characters. Despite the fact that they are portrayed so differently, the relationship between Breezy and Frank is strikingly similar at times to the one between Dave (Eastwood) and Evelyn in Play Misty for Me, which makes the way that the mood is controlled here so interesting. Breezy also introduces a trait often returned to within Eastwood’s directorial efforts, the look at passage of time and the paranoia of not doing the best with it. One monologue at the end of the film forces Frank to question how he is spending his time, and given Eastwood’s productivity and frequent returning to this same point, it’s difficult to think that this monologue isn’t one aimed at himself to a certain extent. 

Next, The Eiger Sanction – maybe his most relaxed film. Feeling like a knock-off James Bond film (the tagline even features an explicit License To Kill reference) from start to finish (in all the right ways!). An action film that just glides along like butter, it’s fun, it’s silly, it’s visually impressive. Eastwood plays up everything that makes his performances so enjoyable, he speaks through gritted teeth for the majority of the film and gets REALLY angry whenever anyone tries to step on his toes, and just like the James Bond films from the same time, he frequently has sex with women who later stab him in the back. Anyone trying to take this one too seriously will probably not have such a good time with it, however, for any Bond fans and any fans of fun action movies, this one is a must. Some of the aerial photography during the climbing sequences are ridiculously impressive, and the film is so entertaining that you may as well just watch it, even if it has nowhere near as much flair or personality as his three previous features.

So, remember when I said that Eastwood soon proved he could do the western genre even better than he did with High Plains Drifter? Well, The Outlaw Josey Wales is that very film. Released in 1976, the film focuses on Josey Wales (surprised?), an outlaw (still surprised?) who loses his family to a savage group of cowboys when they set his house on fire, and decides he will exact revenge on them. Just as revisionist as his last entry into the western genre, Eastwood takes his focus on the cowboy as more of a victim of circumstance than anything else and emphasises it here in a way that has never really been matched. There are so many small moments of real vulnerability here, Eastwood crying and staggering next to his son’s grave, the re-appearing dizzying cinematography during the scene of the tragedy and so many various lines throughout, such as “Dying ain’t hard for men like you and me. It’s living that’s hard when all you’ve ever cared about has been butchered or raped.”, and they are contrasted by Wales’ reputation as one of the most frightening men alive in such a staggering way, especially when Eastwood also includes a large amount of scenes wherein his character saves others and spares people, as well as only ever really killing those who attack him or others in an unfair way. It’s so interesting to see how his perspective on the western genre changed, but I suppose I’ll have much more to say about that when we move onto the 1990s work and get around to Unforgiven! The fact remains, though, that The Outlaw Josey Wales is one of Eastwood’s crowning achievements, and in my opinion deserves a spot amongst the best westerns ever made. 

Moving onto the final film Eastwood directed in the 1970’s, The Gauntlet. It’s no surprise to see Eastwood once again casting himself in the lead role, something he had done in every film he directed up until now aside from Breezy, and even less surprising was the fact that he was playing a badass cop. What is surprising,  however, is just how anti-authoritarian this film is. Some moments in the Dirty Harry films show a similar viewpoint – Callahan often talks about how, despite the fact that he is a rough around the edges, he gets the job done better than anybody else, and Harry also shows a certain level of pride surrounding the way that he never lets himself become corrupted in a corrupt system – and here, it comes together brilliantly  as Eastwood just goes all out against the authorities and gives them the finger. It’s wonderfully pissy, incredibly annoyed for the majority of the runtime which is fascinating given that Eastwood would go on to make some of the most patriotic American films of recent memory later on (I’ll say more about it in the next entry, but his very next film, Bronco Billy, is baffling in it’s juggling between being angry and adoring American life). The Gauntlet is more focused on fun than anger, however, with some of the most fun action set pieces in Eastwood’s career. The finale of this film is just wonderful, the energy is extremely high from start to finish and the anger against authority only really adds to that most of the time. Sondra Locke also makes her second Eastwood appearance of many as Gus Mally, the inciting character in the film who would make many more appearances throughout Eastwood’s work in the 1980s, and also have a key part in his personal life. 

Now to look at the seven films he made in the 1980s. Whilst it is quite likely my least favourite decade/era for his work, there are still a lot of interesting points and, well, we’ll always have Honkytonk Man above all else.
1980 was quite the productive year for Eastwood. He starred the sequel to one of his most popular films with Any Which Way You Can (which follows Every Which Way But Loose) to… some mild acclaim. It was a film that the audience seemed much more pleased with as opposed to the kind of critical reception that Eastwood had often had before. Moving swiftly on from that project, though, Eastwood produced and directed Bronco Billy – a film about a modern cowboy working for a circus/stunt show trying to make a living. Simply put, it is one of his weirdest films. Toeing the line between being a western, family comedy, tragedy, romance, action film… and it isn’t like it just goes through one of those genres at a time, it spends the entire runtime juggling between them all and never really settling. That isn’t to say that the film is as bad as that may make it sound – it really isn’t, it’s quite charming even if it is muddled. Eastwood’s titular Bronco Billy is incredibly likeable most of the time, whenever he acts like a hard-ass it still feels very innocent and just like Eastwood/Billy settling into his cowboy persona a little too comfortably and other than that, he spends the majority of his time just seeming passionate about how he portrays himself to others – like I said, it’s pretty damn bizarre and hard to understand. 

What is most confusing, though, is the ending. This part will feature some mild spoilers, so if you’d want to go in completely blind, skip this paragraph, but it probably won’t damage how you view the film if you haven’t already seen it. Towards the end of the second act, something goes wrong during a show, causing the tent that the cast use to burn down. Now, keep in mind that up until now, the film seems to have been for the most part very anti-American, focusing on Eastwood as some kind of moral saviour in what basically feels like a filthy pit of immoral scumbags. Early on in the film, Sondra Locke (who becomes Eastwood’s assistant later on in the film) marries a man solely for the sake of getting inheritance from her father, and the man marrying her knows this. They get married, she denies him sex and when she wakes up the next morning, he has robbed her and is gone. Eventually, it is said that he murdered her (she has gone missing as she is with Eastwood travelling the country), he is arrested and then put into an asylum as it will make his sentence lighter. Doesn’t that all sound, you know, kind of negative? But what makes this so baffling, aside from the fact that the film still seems unsure whether it is aimed at children or not and then features a film where Sondra Locke’s character is almost raped until Bronco Billy comes to the rescue, is that in the final act, after the tent burns down, Bronco Billy and the gang go and visit a mental institution where they work (for free) once a year, doing a show. On top of the fact that this happens to be the one place in the world where Locke’s husband is (of course it is), what is even stranger is how this outlook of America as some filthy pit suddenly flips entirely. After the manager of the institution has his patients stitch up an entirely new tent for Bronco Billy and his performers, the group return to performing (after a little romantic bump in the road between Eastwood and Locke), and of course, seeing as it is the end of the film after all, everything goes beautifully and the crowd celebrates and Eastwood has enough money for everything to be beautiful and perfect once again, now with the additional bonus of his girlfriend in Sondra Locke. What makes this sudden, maybe overly positive flip even weirder is that, the camera backs out into a helicopter aerial shot that slowly backs away from the tent, and it is revealed that it’s a huge patchwork consistently of a hundred American flags, and as the triumphant music plays, it is not-so-subtly suggested that, if it wasn’t for America, Eastwood would have nothing! It’s absolutely bizarre, even more so given the fact that so much of his ‘70s work took the similar anti-patriotic stance. 

Next up was Firefox, a film that barely feels like Eastwood was involved, despite the fact that he directed, produced and starred in it. This one is really difficult to describe. It seems to be focused almost solely on getting around to the final forty minute aerial climax, but even then, the CGI has now aged so poorly that it’s difficult to take the majority of it even slightly seriously. It’s strangely paced, vaguely entertaining and just leaves a bit of a bad taste in your mouth… I can only really recommend this to Eastwood completionists, and even then I’m reluctant.

Thankfully, next is a real saving grace in Honkytonk Man, released in the same year as Firefox and a film that Eastwood so clearly held close to his heart that it’s difficult not to completely fall for this one. With Eastwood completely switching up his game again, I remember my first viewing of this one being just fascinating. His directorial style changed completely, into something he had never really done before. His one other more tender film up to this point, Breezy, had been shot in a mostly observational, verite way with all of the film’s charm emanating from the characters and the way that they reacted to one another/their surroundings. Here, however, Eastwood’s way with the camera just completely changes – the mood comes from the camera for the first time, something he would continue to do, or at least try to, many times over the coming years. Honkytonk Man is beautiful, and understanding the context and some of the behind the scenes certainly helps to emphasise this. Eastwood explains in Piano Blues (more on that one later!), a documentary he made about… the piano blues… that the blues had always been a huge part of his life, since childhood. The casting of his son, Kyle Eastwood, in the supporting role and the setting during the 1930s (when Clint would have been slightly younger than Kyle Eastwood’s Whit is here, which leads me to believe that this is a story as much about Clint’s discovery of the blues during the Great Depression as it is a fictional story about a musician) also both help to make Eastwood’s own connection to the film much clearer.

Often cited as one of his best performances, Clint plays Red Stovall, a country singer who takes his nephew (Kyle Eastwood) on the road with him for a while. It’s as simple as it sounds – a gentle, beautiful portrait of the 1930s blues scene with many tender moments shared between the two, as well as any supporting characters who wander in and out of the film throughout. The ending is maybe Eastwood’s finest closer (it’s hard to say, though… The Bridges Of Madison County is pretty monstrous too), with it really bringing back the bittersweet tinge that stained the majority of the film preceding it and then emphasised it tenfold. In fact, the ending is mostly just bitter… 
What is also interesting is how Eastwood would come back to do a similar kind of father and son figure film a decade later with A Perfect World (also one of my favourites), however, we’ll have to return to that one in the next part. Though the title and poster alone may serve as deterrents, Honkytonk Man is seriously worth your time. It is one of Eastwood’s most tender, most emotionally expressive, most beautiful films, and even for those who only really care for his work as an actor, it’s worth seeing for his brilliant performance. I still remember kicking myself as soon as this finished for having underestimated and avoided it for as long as I did.

Next on the agenda, Sudden Impact. The fourth entry into the Dirty Harry series, which had been quietly carrying on in the background during the last twelve years (this one was released in 1983), and the first entry that Eastwood directed, follows a young rape victim (played by Sondra Locke) and Dirty Harry’s pursuit of her when she decides to enact revenge on those who attacked her and her younger sister. With Eastwood at the helm, this one really stands out in comparison to the other Dirty Harry films. Callahan himself is treat completely differently, and for the first time in the franchise the morality of the police is brought into question. It’s an outright ugly and dark film, too, which takes away from the usually sunny and quite cheerful previous entries and emphasises the fact that Eastwood is here to make the franchise his own (the influence of his style here can be spotted all over the place in the last Dirty Harry film, The Dead Pool, with much of that film also taking place at night, including the wonderfully silly final set piece).
Sudden Impact is, frankly, a rough watch at times. Eastwood has always been good at capturing trauma on screen, as I said with The Outlaw Josey Wales’ jaw-dropping opening sequence, and it shows here once again when, in flashback, we return to the rape sequence that set Sondra Locke on her revenge mission. Is Eastwood really the hero for trying to stop this woman? Should her violence be allowed as, after all, she was the victim first? It’s just crazy how Eastwood takes what was becoming a gradually sillier franchise and completely grounds it again, forcing into question American law morality. Much of the violence in the film is stripped of fun here, too, leaving a nasty taste in your mouth instead of a kind of joy at seeing Callahan succeed. The violence feels empty, maybe not unnecessary but it feels gratuitous and saddening. A surprisingly good film, coming from a series that was slowly  dying. Whilst Sudden Impact didn’t seem to revive it for everyone, it certainly made me perk my ears up again. It’s far from perfect, but it is fascinating, especially when compared to the other Dirty Harry films that had been coming out over the previous twelve years.

Two years later, Pale Rider released. The 1980’s wasn’t really a good time for westerns. With the Hollywood New Wave came the death of the western, and Star Wars has been the nail in the coffin, really – taking the characters and the story of a western (okay, it comes from Kurosawa, but samurai films are similar to westerns, too) and adapting it to a newer, more exciting (for many) setting. Pale Rider is mostly interesting contextually, looking at how Eastwood changed his portrayal of the western hero overtime, with moments such as The Stranger refusing sex with a young woman, which would have been normal at the time, and also the representation of the western protagonist as a kind of Devil, despite the fact that his character is a preacher. As the tagline says, ‘and Hell followed with him’, and it definitely does here, with some of Eastwood’s most satisfying action scenes to date featured throughout. It’s a good film, admittedly. It feels a little lacking when compared to Eastwood’s 70’s westerns, the high points of The Outlaw Josey Wales and High Plains Drifter, but it’s still worth watching. It’s one of the best westerns of the 1980’s, even if that isn’t really saying too much, all things considered.

Next up, Heartbreak Ridge. Eastwood’s first shot at making a film involving the army (explicitly, at least), and it’s a mostly laid back one. Releasing one year before Kubrick’s Full Metal Jacket, this film honestly feels like the first half of Kubrick’s film made into one. It’s full of the typical Eastwood traits – bitter old man speaks through gritted teeth for the majority of the runtime – and it also follows the majority of the clichés of the typical army training film, with the one liners (“If I was half as ugly as you, sergeant major, I’d be a poster boy for a prophylactic.”, is a personal favourite), the camaraderie and the overall rather cloudy look at war which is admittedly a little hard to swallow. Many seem to be quite offended by this one in general, with Eastwood’s character being slightly more of a hardass than he usually is (now that’s saying something!) and often using… questionable slurs, being a manipulative ass and just being awkward, but it’s always played off in this innocent way, strangely. What I wasn’t expecting was the switch, which rears it head towards the end. The fun and games occasionally stopping to make way for this more nuanced look at how Eastwood’s mind has been warped by his experiences in the war, or at least, that’s what I took it as. It’s uncomfortable to see, with the film feeling like this collection of hazy memories frequently interrupted by these nightmarish moments of manipulation and trouble. It’s absolutely fascinating. It isn’t the most interesting of his military based films, but it was one hell of a way to kick things out of the gate. He ran before he walked. 

Ending the decade on another intriguing detour, Bird came out in 1988. The film stars Forest Whitaker as Charlie Parker in a biopic that follows his drug addiction and alcoholism, his family life and his music with a close eye. The film feels quite directionless, meandering – sometimes in a good way, but sometimes it detracts from the emotional beats quite a bit. Sometimes the lacking focus on story leaves room for some beautiful character moments, such as the ending (my God! What a fantastic ending!), but other times it just makes the film feel much longer and aimless. It’s an intimate portrayal of Bird, one with plenty of scorn where necessary to the point that you can tell Eastwood respects him greatly. The focus on Chan, Parker’s wife, is also fascinating, but the potential that the film has to be a touching, important biopic is so often lost to the meandering plot. It remains a fascinating set up to Jersey Boys, a film Eastwood made about a group of singers later on, and also as the second time that Eastwood revealed his deep love for music after Honkytonk Man. This time wouldn’t be the last, either.

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.

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.

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.

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.

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?

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. 

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. 

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.

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.

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. 

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.

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. 

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. 

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.

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. 

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!

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. 

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 containing some of his best films with his least exciting one to date, however, I suppose it can’t be helped.

So, we are very nearly caught up to date with this investigation of the films of Clint Eastwood. There are just seven films left, the majority of which are fascinating, so without rambling, let’s get straight into it and see how he continues to evolve as a director, somehow always managing to keep up with the youngest, most ambitious directors around at any given point. 

It’s time for a big one, everyone. Hereafter, released in 2010 and starring Matt Damon in the leading role, is Eastwood’s weirdest film to date without a doubt. That’s right, not even a voodoo focused crime comedy period drama has anything on this. Hereafter follows three main characters, an American man (Matt Damon), a French journalist (Cecile de France) and a young English boy (George McLaren), but this triptych focus isn’t even the strangest thing about it (though, it is absolutely worth reflecting on the fact that Eastwood has evidently taken inspiration from Alejandro Gonzales Inarritu, which is fascinating to me as they’re two of the directors I think I would be easy likely to ever associate with one another), what is stranger is the focus of the film on the afterlife. I had never pictured Clint Eastwood as a very spiritual person, given his films and his typical hardass character, his general attitudes and even because of his age it seemed unlikely or unexpected, but Hereafter is a stunningly tender, mind-warpingly beautiful film looking at death and the ramifications of death on these different characters, all of whom have direct contact with it within the film, specifically Matt Damon, who can see the spirits surrounding someone as a psychic, these spirits giving him information about themselves, with these visions occurring any time he so much as touches the skin of another person. It does sound ludicrous, absolutely, but it is handled in such a stirring, poignant way where the contrasting between life and death is so touching, and it is a story told with such conviction that it has to be admired. The performances are fantastic, especially from Matt Damon and Bryce Dallas Howard (who is mostly involved in Damon’s storyline), and the observations of how death or loss directly affects each and every one of us is one of the most interesting presentations of such a topic that there has been in quite some time. This is one of Eastwood’s least popular films, but not only is it one of his most fascinating from a directorial perspective, it is one of his best and most touching films, if not the best. You’d be hard pressed to find better representations of death in cinema.

The year after, J. Edgar came out, a film starring Leonardo DiCaprio as – you guessed it! – J. Edgar Hoover. I personally don’t think too much of this one, but it is very interesting in so far as its presentation of such a respected American figure. Many have called Eastwood racially insensitive and/or too heavily focused on warping his films into American propaganda, but here it becomes clear that he is doing anything but. In J. Edgar, Eastwood presents the story as the characters involved would have seen it as opposed to how Eastwood sees it, or how the audience would see it if the story was told truthfully. It’s a bizarre film too, with shoddy make-up that is really quite distracting, but also slightly endearing for one reason or another. It’s difficult to pin down, as there are so many different things going on here and in spite of all of that, the film still feels really quite stagnant and slowly moving at times, with not enough interest in the character as so much is told so quickly, and what is actually withheld comes as very little surprise later on down the line. It has to be said, though, that DiCaprio is a force of nature in his performance here, and Armie Hammer does a terrific job too, not that good performances from either of those should come as any kind of a shock. It’s an interesting film as far as looking at Eastwood’s politics in his films goes, but other than that I must say this is one of his less remarkable films, probably not one that everyone could enjoy. 

After a three year break, Eastwood returned in 2014 with Jersey Boys and American Sniper. For the sake of continuing to keep the chronological focus in check, we’ll look at Jersey Boys first. I personally would never have expected Eastwood to direct an adaptation of a musical, but here we are. And it just so happens that he is damn good at it. Focusing on the turbulence typical to the biopic genre, the film documents the rise and fall of The Four Seasons, a group of musicians made consistently of, you guessed it, four boys from Jersey. As someone who hadn’t even heard of the band before seeing the film, it is admittedly very difficult for me to speak of the authenticity of Eastwood’s portrayal of the group and of their lives, however, fans seem to agree that the film is really quite accurate and intricate. What is astounding to an outsider, however, is the control Eastwood has in assisting his audience to look directly, and deeply, into the hearts of these characters, who start off as teenagers looking to have some fun, make some money and impress women aplenty and end as calloused men who have seen both the positive and the negative aspects of the oh-so-alluring world of show business. Delicately capturing the nuanced pain of each and every character, the film plays as a surprisingly straight-laced and well controlled look into the actual characters, rather than making the cliched mistake of playing the best songs by the musicians the film is about whilst the character act out the tiniest of melodramas in the background to the soundtrack (usually for the sake of selling some CDs). Each and every one of the main four feel alive, especially Frankie Valli, the group’s frontman, who acts as the protagonist of the film and is played brilliantly by John Lloyd Young. It isn’t a particularly revealing film in terms of its director – Eastwood, as is typical of the films of his that he doesn’t find himself starring in, takes a step back and allows the story to speak for itself – but that doesn’t mean that it isn’t illuminating of his style and his passion towards the music the film looks at. It’s also generally quite interesting to me that the film does look so in-depth at the behind-the-scenes of the band, focusing more on their daily lives than their stardom in a way that seems to suggest that maybe Eastwood wishes people could see his daily life more. I may be reaching, but the level of focus on the mundanity of celebrity life is fascinating.

As I already said, American Sniper also came out in the same year. Starring Bradley Cooper as U.S. Navy Seal Chris Kyle, the film focuses primarily on his time spent as a Sniper in his four tours of Iraq and the rippling effect that this has on his home life when he is there. This is one that seems to really divide an audience, which is simultaneously quite surprisingly given that the film is so powerful in its storytelling and so interesting in terms of the points it starts to make about America and their attitude towards war (something Eastwood would double down on with 15:17 to Paris, to even more scorn than before), but also understandable in so far as the real Chris Kyle was kind of a prick and so many people have an instinctual reaction to cringe at the thought of the Iraq war. It’s a shame, as there is certainly an outstanding film in here once you can get past some of the more obtuse parts of it, such as the often-cited in memes prop baby and some of the lines that take quite nuanced conflicts and turns them into overly simplified one line debates between family members to be subsequently forgotten about. 
The most interesting point made here is the looking into American Imperialism as something terrifying even to those from America. It looks at imperialism as something that ends badly for literally all involved, from the deaths of children in Iraq to the never-ending aftermath that comes from imperialism. Kyle, at least within the content of the film, is a victim of circumstance – a man bred to being a terminator, an emotionless killing machine to serve his country – someone programmed from birth for one specific purpose by everything surrounding him, and then used, squeezed until there is nothing left but an empty sack of the person who once was Chris Kyle, and thrown back into a society with the expectation to remain just as emotionless as he has been psychologically programmed to be from birth. His emotion is seen as weakness, so he hides it. His fear is weak, his difficulty and hesitance to make rough decisions is a weakness, and these weaknesses must all be lost because with them he cannot serve America to the best of his potential ability. Let’s not forget, Kyle joins the war because of what he sees in America and nowhere else, and that America made the issues with Iraq out to be smooch worse than they really were to the point that so many people were pro-invasion.
Spoilers incoming too, but the ending really places the hard emphasis on how this Imperialism is destructive to everybody. The death of Kyle is much more symbolic than it seems, and can easily be applied to just about any single American soldier during the Iraq war (or facing its rough aftermath). The American flag teeters past sheepishly, proving the death of a servant to America, and yet beyond the inclusion of the flag, America doesn’t care. They bred Chris Kyle and led him directly to his death, as Imperialism has done to so many other men. 
It’s certainly one of Eastwood’s sharpest films, and the way that the focus on the Iraq war is played from the American point-of-view to this degree definitely makes the entire film a much harder pill to swallow than it really needed to be, with Eastwood’s direction sometimes threatening to slip into being proud of America for the war effort when it is trying to make the audience sympathise with Kyle for being cultivated by all of this media surrounding him for the entirety of his life.
Personally, I think that in the case of the film a lot of people are too fast to ignore the way that Kyle, and most soldiers for that matter, are manipulated into their beliefs by the powers that be, and that they really have very little control over finding these beliefs simply because of where they live. The film doesn’t frame Kyle as the only victim of the war, it doesn’t make him any more important than any of the numerous people whom he kills throughout his four tours, it simply makes him yet another victim of these ruthless American ideals, a victim of his circumstances in the very same way that the people in Iraq were. It’s a terrifying and truly devastating film, one that is often quite difficult to watch and one that deserves so much more praise that it has received up to this point – I can only hope that with time more come to realise the true intentions of the film and are able to see what it was that Eastwood was really trying to illuminate with the film, but only time will tell.

After two more years, Eastwood returned with Sully, another true story of recent American heroism. This time following Tom Hanks as Captain ‘Sully’ Sullenberger known for the ‘Miracle on the Hudson’ in January 2009, in which he landed a damaged plane on the Hudson River saving the lives of every single passenger of the 155 on board the plane, the film is mainly focused on what occurred after this unpredictable miracle moment, looking specifically at how Sully was actually maligned for his actions, with his superiors claiming that they were unsafe and that he may have to go to jail for choosing to land the plane in the way that he did despite the fact that he had saved the lives of over one hundred and fifty people. It’s a very carefully controlled film, one that takes its story at a surprisingly leisurely pace and is much more focused on the discomfort of the world at large when the right thing turns out to be the opposite (or is made to look that way by others). Hanks is great, and the culminating courtroom scene is priceless in terms of just how satisfying it is to see Sully tackle the arguments thrown his way. It is interesting particularly in how it contrasts the rules of certain organisations against the ‘rules’ of instinct – the rules of the airline that Sully flies for evidently don’t have humanity in their eyesight, only following rules and regulations. Sully, for being humanist and acting on the instinct to simply save himself and the others on board, is punished severely for abiding by the wrong set of rules, according to some anyway. It isn’t an absolute must-see, but it is a startlingly strong film by itself. 
In 2018, Eastwood did yet another pair of films within the same year. Somehow, even at the age of 88, he puts out more films than most directors. 

The first of these two films was the aforementioned 15:17 to Paris, a film that follows the lives of three American men who, in August 2015 stopped a terrorist on a train in France who was carrying enough ammunition to kill over five hundred people. To contrast Sully quite effectively, this one shifts focus and looks at what leads up to this heroic act and, furthermore, it uses the real people involved in the ordeal as the actors to add to the authenticity of what we see. It’s an absolutely fascinating film, far from perfect but so inexplicably interesting that it’s hard to really care very much about the visible flaws and issues at the centre of the film. Viewing the boys as children and then seeing how their differing life experiences end up bringing them together is interesting by itself, but when paired with Eastwood’s distinct Americanism and his focus on the way that violence is seen in contemporary America, it starts to fold out into something all the more entrancing. As I said, it is FAR from perfect, and this deserves to be emphasises, but it’s a film testing out a kind of gimmick so ballsy that I can’t help but admire this one deeply, especially coming from a director as seasoned as Eastwood is. It was Tarantino who once claimed that directing is a young man’s game, but evidently that is just another thing that he is wrong about – Eastwood is living proof that, if anything, some directors can only improve with age.

Finally, or at least finally for now, is the Mule. Eastwood’s second film released in 2018 (or early 2019 in the U.K.), a more than suitable swan song for Eastwood’s career. It’s a strange film, going from looking at Eastwood’s politically outdatedness in a comical light to looking at the various downfalls of protagonist Earl Stone who has too often left his family behind in trying to focus on his business… sounds familiar, doesn’t it? For such a self-reflexive film, it is surprising that Eastwood does go quite as deeply as he does here – don’t get me wrong, this is no All That Jazz, but it is shockingly probing for something from someone who comes across as jaded as Eastwood does more often than not. It’s not personal to any kind of alienating degree either, but just enough so that we can understand and empathise even if we see exactly why Stone lands in the situations that he does. It’s certainly a touching film, one that evidently speaks volumes about how Eastwood feels about himself and about his focus on his work and lack thereof on his family, and it just seems to fit perfectly into the puzzle of his filmography as an ending. However, he has already started working on another film, set to release this year or next, so it won’t be his last!

So, that brings us to the end of Eastwood’s work, for now at least. It’s certainly a mixed body of work, one that ebbs and flows in a pretty blatantly rampant way, but it’s coming from one of the truly defining film stars, which adds a great deal of significance as this filmography acts as a kind of emblem to modern mainstream Hollywood, or more so the changes that have occurred not only within Eastwood as a director but Hollywood as a whole. The same can definitely be said for his career as an actor, but it may take a bit longer to wade through all 150 of his starring roles. Anyway, enough rambling – I’m looking forward to seeing what comes next from Eastwood, and curious to see how it contributes to the shape of his overall filmography. 

And just for fun to close, here is a ranking of his films. I know that throughout this piece I’ve called many of his films some of his best, but consider that this has been written over three months and that the ranking has changed greatly during that time! Without further ado:

1. Letters From Iwo Jima
2. Honkytonk Man
3. Absolute Power
4. Mystic River
5. Million Dollar Baby
6. Unforgiven
7. American Sniper
8. The Bridges of Madison County
9. High Plains Drifter
10. Hereafter
11. The 15:17 To Paris
12. Play Misty For Me
13. The Outlaw Josey Wales
14. Changeling
15. Gran Torino
16. A Perfect World
17. White Hunter, Black Heart
18. Breezy
19. Flags of Our Fathers
20. Sully
21. The Mule
22. The Rookie
23. Sudden Impact
24. Jersey Boys
25. Blood Work
26. The Eiger Sanction
27. J. Edgar
28. The Gauntlet
29. True Crime
30. Pale Rider
31. Heartbreak Ridge
32. Piano Blues
33. Space Cowboys
34. Bird
35. Bronco Billy
36. Midnight in the Garden of Good and Evil
37. Invictus
38. Firefox

EDIT – Since writing this, Richard Jewell released. Here are my thoughts on that film!

This review contains some spoilers for the 15:17 to Paris and some spoilers for Richard Jewell (although mostly they follow the known story of the real events! So if you know of those, you should be fine!)

I have to admit it – at first, I was very confused by what I thought about Richard Jewell. I mean, where does a film stand when it is focused on the story of a man doing the right thing once, who has an evidently destructive and questionable past, getting caught up in an FBI investigation. I have to say, I was quite fixated on the political leanings, and so when it turns out that Jewell owns stacks upon stacks of guns and that he is so enamoured and/or intimidated by the FBI that his reaction to their obvious attempts to frame him for the Centennial Park bombing is to be entirely submissive and compliant despite the fact that his life is on the line. Initially, I was mostly confused and also slightly frustrated by this almost comical presentation of Jewell as a centrist of some sort, but after some thought, I clicked with what Eastwood was really trying to say about modern America, specifically about the power held by the Government and by the FBI.

As Sam Rockwell’s Watson Bryant directly tells Jewell upon the question ‘How can they do this?’ that the FBI can derail a life ‘Because you’re nothing’, it suddenly becomes clearer. And there’s no doubt that the line “I fear government more than I fear terrorism’ also clearly spells out a thing or two about what Eastwood is trying to do here. Let’s not forget that one of his most recent films, The 15:17 To Paris (2018) also tapped into the true story of a group of typical ‘great American heroes’ who we see grow up with the illusion of the American Dream and of patriotism through warfare/the fight against terrorism, etc, and that in that film they actually do getaway from the situation (mostly) unscathed. There is a clear mismatch in the ideas at play, and whilst in The 15:17 To Paris the heroic action occurs outside of America and only after the boys have come to realise that some, or even the majority, of what they were told about America and even the war on terror as children was untrue, in the case of Richard Jewell, Richard is still completely blind to the realities of his situation, and his heroic action occurs in the heart of America (especially seeing as it is set during the 1996 Olympics, which only adds to the spotlight on America specifically).

The dynamic created by this difference is so clear. The 15:17 To Paris ends with the typical fanfare expected, and unsurprisingly the film was mostly disliked for its treatment of the heroes (okay, the acting is pretty bad too, but these people aren’t professionals…), and whilst Richard Jewell may technically have the happy ending of Jewell being free, there is something much darker and much more unexpectedly ominous bubbling away underneath, coming from the nuances like the scenes of clear trauma and even the text cards that close the film and say that Jewell passed on in 2007 due to heart failure, whilst a few moments in the film imply that these issues really started due to his ruthless treatment from the FBI and from the media. It is the same nuances that really get to what Eastwood is trying to say, too – that Richard Jewell is a victim of America. He has been brought up, as he says himself directly to the FBI, to believe that to be a member of the United States government is the highest calling a mortal man can receive, and he spends the majority of the film clearly under American tradition – he owns those stacks of guns I mentioned earlier on (that initially had me confused about the political leanings of the film, but become clearer under this lens), he is so infatuated with the idea of being involved in Public service, when the media confronts him he is excited and open to doing whatever they say (and the same can be said for the FBI, despite their clear and repeated attempts to deceive Jewell) – and yet all of these things cause narrative trouble for Jewell as he finds himself falling deeper and deeper into disillusion and denial.

Richard Jewell has been sold the deceptive American Dream since birth, much like a lamb to the slaughter. It comes through with his idolising of American iconography, in his need to own (a lot of) weapons, in his admiration of the FBI, the government and the media, in his want to have power (shown mostly by the scene towards the start of the film that sees him get into trouble for going outside of his jurisdiction in an attempt to stop crime whilst working at a University), and in so many other things, too. And it becomes clear to the audience quite early on (after Richard’s change in views on power and how it should be used, or even how it should be measured) that America is not the place for Jewell’s humanitarianism, or the humanitarianism of anybody else for that matter. It is too focused on how things look from an outside perspective, and the power of the media and of the government also means that people alone don’t stand a chance. Of course, Eastwood’s looking at the deception of the American Dream, particularly when involving war, is nothing new, and neither is his focus on people getting into trouble (DEEP trouble) simply for doing their jobs in an exemplary way (I’m looking at you, Sully!), but this overarching focus on power hierarchies in America and how they can make these positive actions mean nothing is genuinely the most caustic Eastwood has been towards America in his entire career (maybe with the single exception of Letters From Iwo Jima, though this one is more focused on America’s self destruction). Let’s not forget, the man is 89 years old, and has most definitely seen it all, and so he knows plenty about his home country. The fact that he is able to take this story of just one man faced with the power of the media and the government, and that he is able to also show that Jewell has been framed from his birth by the government into being essentially radicalised by America itself (the questions thrown at him by Rockwell’s Bryant about extremist groups are brilliant. Jewell’s emphasis on saying that ‘I don’t like those groups’ despite being part of the biggest one on Earth is a great moment), only goes to show that Eastwood most definitely still knows what he’s doing.

I also can’t not talk about the moment when Jewell says to the FBI that their actions have only worked to place fear into and to effectively stop people in the future from reporting such issues as potential terrorist threats. In fact, the entire ‘courtroom’ scene is just brilliant as we finally see Paul Walter Hauser’s Jewell come out of his shell and realise what has happening to him because of the ideologies he has been sold his entire life. And what a performance Hauser gives. The same can really be said for the entire cast, but I found that Hauser especially perfectly held in this disillusionment and this uncertainty that comes with the realisation that the ideas you’ve been brought up to understand as patriotic and positive are the exact opposite. Jewell cares for people on both a personal and a collective level, and is almost killed for this belief simply because the FBI know that they have the ability to quieten their bosses and avoid trouble in doing so.

As the brilliant Filipe Furtado says, Rockwell’s Watson Bryant is essentially Eastwood placed into the film as a character (Furtado’s point of Rockwell even essentially ‘directing’ Jewell through his court case blew my mind a little, I must say!), which also makes things more interesting as he places himself in the role of the saviour (I feel like the only reason Eastwood himself didn’t play the part was the issue with age and authenticity, but who can really say other than Eastwood himself?). In fact, the focus on the supporting ensemble is brilliant, with each character being seen through such a specific perspective that they could easily become nothing more than empty stereotypes, but Eastwood’s direction elevating the majority of them to something more. I do think that Jon Hamm’s Tom Shaw is a little too one dimensional, especially when he reveals that he knows Jewell isn’t really the culprit but still thinks he’s ‘guilty as hell’ just due to his profile and background, but other than that I think Eastwood gives plenty of space to each character to allow the audience to see the effects that America has had on each of them individually. Jewell and mother Bobi (played by Kathy Bates, who doesn’t get enough screen time for my liking but is great in her scenes!) are both victims of deception and extreme confusion at the hands of the government, Bryant has already figured things out but is still amazed by the toxicity at the heart of his country and Olivia Wilde’s journalist Kathy Scruggs, whilst really quite cold and merciless towards Jewell at first (due to a focus on attaining power and money, two more American ideals!) is also given the time to change when she too realises that she has been sold a lie by not only herself but by the FBI. (I’m not sure why so many seem assured that Eastwood is framing her as the villain of the film when he dedicates an entire scene to her change of heart, and Jon Hamm’s grizzly detective is the one to leak information and to remain assured that Jewell is in fact guilty even after the FBI let him loose… but oh well!)

I think that Eastwood has really managed to sum up his work from the last few years here, and even if I don’t think that this film is quite as good as Sully (2016) or American Sniper (2014), I do think that it is very revealing of Eastwood’s ideas and it is completely fascinating to look into! Reading about and discussing the film has been really interesting, and I’m definitely willing to talk about it more if anyone has any thoughts – I have written more here than for any individual film in quite some time, and have to say I still feel like I’m missing quite a bit… but such is life! Thanks for reading!

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