Ranking ALL 41 Films Directed By Clint Eastwood

Alex JosevskiDecember 24, 2024n/a89 min

Clint Eastwood’s Juror No. 2 is now streaming on Max (in the U.S.) and Crave (in Canada). Given the film’s insanely limited theatrical release last month, now most audiences will have a chance to see the film. Though some have dubbed it as his “final film” (a notion I’d challenge given his work ethic even at 94), Juror No. 2 is the 40th film he’s directed over the course of a career spanning over five decades. As one of Hollywood’s most enduring icons and last living legends, and one who serves as a bridge between the classic era and the modern age, Eastwood’s filmography has covered a remarkable range of genres and stories. Read as we explore and ranking each film from his extensive body of work.

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41. Invictus (2009)

Based on the true story of the 1995 Rugby World Cup Championship, Invictus follows the early reign of Nelson Mandela’s (Morgan Freeman) presidency and he attempts to rally South Africa’s rugby team (led by captain Matt Damon) to victory as a way to bring the country together. While not a terrible or especially egregious film by any means, Invictus earns its spot at the bottom for sheer dullness. It’s a film that’s as workmanlike and technically competent as any Eastwood project is, but lacks in the thematic heft that defines his best work.

40. J. Edgar (2011)

This biopic follows the life of J. Edgar Hoover, one of the most influential, and infamous men in US history, whose revolutionary law enforcement techniques led to the formation of the FBI and whose paranoia and conflicted private life made him a power hungry monster. Led by Leonardo DiCaprio as Hoover, you wouldn’t be blamed for initially thinking this to be a Scorsese project (oh how I wish it were so). While the material is ripe for Eastwood, an examination of the corruption at the root of America’s systems, and the false mythologies spurred by Hoover in crafting the ideal hero “men in black” agent, the film is unfortunately a real bore, never quite finding the right angle to latch onto and getting lost amidst the sheer breadth of history that Hoover lived.

39. Jersey Boys (2014)

Adapted from the famous Broadway musical, Jersey Boys is surprisingly not a musical, instead turning the material into straight forward biopic of Frankie Valli and the Four Seasons. I’ve never seen the original stage show but I’d be surprised if it’s as grounded and moody as Clint’s version. The sombre quality afforded to it, specifically in its ruminations on the passage of time and how fame costs you your family are all hallmark themes in Eastwood’s late films and have been better tackled elsewhere. Jersey Boys is most notable to me for the meta dimensionality of the scene where the Four Seasons watch a young Rawhide-era Clint Eastwood on TV.

38. The Rookie (1990)

Two years after hanging up the iconic Dirty Harry role with The Dead Pool, The Rookie sees Clint back in very familiar territory as a grumpy, take no shit, hot head detective. Unlike the grittier Dirty Harry films, the film sees Clint operating in pure popcorn entertainment mode, as evidenced by his pairing with Charlie Sheen and the explosive action set pieces. Clint could do this role in his sleep, he’s a natural at it but that auto-pilot quality extends to the entire film, competent but lacking in passion. A fun turn your brain off programmer that I’d gladly watch again if I stumbled on it on TV, but it’s not a film that’s likely to leave much of an impact.

37. The Eiger Sanction (1975)

Notable for being the most problematic film ever made. The Eiger Sanction follows Clint as Jonathan Hemlock (one of his better character names), an art professor who sleeps with his students, art thief, and professional assassin who works for an albino former Nazi. His target? Only accessible on the dangerous Eiger mountain range. Buoyed by a truly bonkers series of plot events and bizarre characters (played by great character actors such as George Kennedy and Jack Cassidy), gorgeous nature photography, and stunning stunt climbing sequences, The Eiger Sanction gets bogged down by lumpy pacing and an overlong runtime, making this more dull than exciting. The Eiger Sanction is one of those films that’s more fun to talk about than actually watch.

36. Breezy (1973)

In what’s likely Eastwood’s least seen and least known about film, Breezy depicts a May-December romance between the titular Breezy (Kay Lenz), a free-wheeling young hippie and Frank (William Holden), a middle-aged man. The clash between the counterculture and the establishment she’s supposed to be rebelling against adds some interesting wrinkles to what is otherwise, a fairly slight film.

35. Heartbreak Ridge (1986)

Heartbreak Ridge is Clint in top “grumpy old man” form as a hardened Marine sergeant tasked with taking command of the trouble making platoon while clashing with his superiors and ex-wife any chance he gets. Much more of a comedy than anything (think the first half of Full Metal Jacket if the boot camp was less horrific) with a litany of creative insults and one liners dropped a mile a minute, his chemistry with a young Mario Van Peebles is a particular highlight leading to many laugh out loud moments. Aside from that, it is a fairly generic watch, hitting all the tropes and clichés one might expect from one of these.

34. Mystic River (2003)

Mystic River follows the lives of three men (Sean Penn, Kevin Bacon and Tim Robbins), former childhood friends all bound by past and present traumas. The film presents yet another Eastwoodian mediation on violence and masculinity, the intergenerational impacts on self and community that violence can bring and the inherent destructive ideals of masculinity that buries such pain until it explodes out in ugly fashion. An oppressively dark watch at times, it is certainly an impactful watch albeit one which comes across slightly disinteresting in its aims for legitimacy. The beginning of Clint’s prestige era.

33. Firefox (1982)

One of the few special effects driven blockbusters Clint has made, Firefox follows ex-Vietnam pilot Mitchell Gant (Eastwood) is sent into the Soviet Union to break into and steal the titular Firefox, an undetectable new jet place controller by your mind. For a premise as silly as that, it’s quite surprising how grounded most of this film is. The first 2/3 follows Gant as he goes undercover to infiltrate the Soviets. His PTSD and inexperience doing the spy work adds a lot to the tension as he evades capture and double agents across the way. Critics at the time derided Firefox for taking too long to get to the plane action but I’d argue the film is far more entertaining in its slower, spy thriller half.

32. American Sniper (2014)

Eastwood’s biggest financial hit, and one of his most controversial, American Sniper is a biopic of Navy Seal Chris Kyle, the most lethal sniper in US history. Continuing his deconstruction and examination of masculinity, heroism and the mythologizing of said heroes, American Sniper is a disturbing, and oftentimes fascinating examination of the culture and society that breeds such men albeit one I suspect would achieve its thematic goals more effectively if it weren’t about a real person, which regardless of intent does mythologize him inherently by the medium. Following Kyle’s life from childhood to his untimely death, Eastwood highlights how violence is passed down from father to son, violence as a threat and necessary tool to protect others. God, Country, Family becoming his catchphrase and the signifier of the cultural identity that makes a man like Chris. A cultural identity that also needs to make heroes of men like him to justify the violence and destruction of war. Anchored by Bradley Cooper’s best performance, American Sniper is a rock solid Eastwood film that lays the foundations for his late era themes.

31. Midnight in the Garden of Good and Evil (1997)

Clint’s first Savannah, Georgia set legal drama before Juror No. 2 and one of his most uncharacteristic efforts. Based on a true story, Midnight in the Garden of Good and Evil covers the murder case of Jim Williams (Kevin Spacey), an art dealer who claims to have killed his lover in self-defence, and the John Kelso (John Cusack), the out of town city news reporter entwined in a bizarre mystery and machinations of the town. Set against the Southern Gothic backdrop of Savannah, we get a truly unique ensemble of characters, voodoo priestesses, men who walk invisible dogs, people who take flies to themselves, and the iconic Lady Chiablis (playing herself), one of the first prominent trans actors in a Hollywood production. You can tell for her scenes that they just let the camera roll as she does her thing, and she completely steals the film from everyone. In what would otherwise be a standard true crime courtroom drama, Eastwood’s focus on the town, atmosphere, and daily lives of the community gives it an almost hang out quality at times, dropping us into this world so immersively.

30. Bird (1988)

Bird is a music biopic about jazz legend Charlie Parker (played brilliantly by Forrest Whittaker) and is among the more radical musician biopics I’ve seen. An underrated Clint factoid is that he’s a total jazz fanatic, and that adoration for the culture and music is very much felt in this passion project. Breaking convention and cliché, Bird takes on a stream of consciousness free flow through the narrative of his life story. You don’t get a Wikipedia synopsis of all his major life events, but you do get a sense of who he was as a man. I’m a novice when it comes to the jazz scene and am especially clueless surrounding its history which kept me at a slight distance with Bird. Still, it is host to some of Clint’s most stylistic filmmaking and is a must watch for any jazz fan.

29. Blood Work (2002)

Clint playing the hits in another pulpy action thriller as a grumpy old man. Blood Work sees Clint return to a familiar archetype but now plagued with old age as a retired FBI profiler brought back on to solve a new serial killer case. Having recently suffered a heart attack and subsequent heart transplant operation, he’s still the hardass anti authority Clint, but needing to temper himself somewhat per his doctor’s instructions. It’s nothing you haven’t seen before, but Blood Work is a solid and entertaining watch that offers up a fun twist on the serial killer dynamic.

28. Space Cowboys (2000)

Aside from Firefox, this is Clint’s other foray into “sci-fi” and VFX driven spectacle, but one with a surprisingly emotional core to it amidst the old guy hijinks. Space Cowboys is pure wish fulfillment and audience pleasing silliness that sees Clint and the boys (Tommy Lee Jones, Donald Sutherland and James Garner) go up into space to save the day! 40 years after Clint and his team were turned down to be the first men in space, they’re brought back into the fold by NASA when a cold war era satellite is tumbling towards Earth. The issue? The coding on board to stop it can only be understood by Clint, none of these young guys can read it. Very cheesy, very silly but so fun and with a heartwarming final image. A total dad movie.

27. (BONUS) Tightrope (1984)

Wait, but isn’t this film credited to Richard Tuggle? Yes it is, but by all accounts (and viewing the finished product) Clint ghost directed this film. Tightrope follows detective Wes Block (Eastwood) on the hunt for a serial killer targeting prostitutes, the catch? They’re all prostitutes that Block himself has been sleeping with. Wholesome family man on the streets, kinky freak in the sheets, hei finds himself descending into the seedy underworld further and further than he’s ever gone before. While the premise may not be particularly unique, Tightrope is notable for being one of the early examples of Clint starting to deconstruct his image and delivers on some good, sleazy thrills.

26. Flags of Our Fathers (2006)

The first half of Clint’s World War II duology of the battle at Iwo Jima (the other being Letters from Iwo Jima). The first tells the story from the American perspective, in particular the famous photo of the soldiers raising the flag up on the hill. Flags of Our Fathers is a tear down and indictment of the type of hero narrative often seen in war films, mediating on the power of images and their role in the mythologizing of war. Flags follows three of the soldiers who raised the flag, brought back to America to promote the sale of war bonds as we flash forward and back to the war and its aftermath. The juxtaposition of the harsh brutality of war with the sanitized propagandic images the government wishes to spin out of it is quite effective. In one particularly poignant scene at a fundraiser, one of the soldiers breaks down, grieving together with one of the gold star mothers before being told by organizers to take this outside, outside of the view of donors and the media. It’s hard for people to grapple with the sacrifices made by these men, so we put them up on a pedestal to deify them, thus robbing them of their humanity. An essential Eastwood text on his key themes whose only major drawback is being compared to it’s significantly better companion film. More on that later.

25. The Gauntlet (1977)

The Gauntlet sees Clint end his 70s run with a (literal) bang. Clint plays Ben Shockley, a washed up cop with a drinking problem so bad that bottles of liquor pour out every time he opens his car door. Tasked with escorting a witness (Sondra Locke as a smart ass prostitute) from Vegas back to Phoenix, what should be a routine job quickly escalates into all out war across the US, as the unlikely duo are chased by bikers, cops, and the mob. While lacking in some of the thematic meat of his other films, The Gauntlet delivers on its pulpy action packed thrills with a likely world record for number of bullets fired in a single film. The titular gauntlet set piece is a truly epic gluttony of gunfire and explosions.

24. Play Misty For Me (1971)

Eastwood’s debut film is an unlikely one for the filmmaker we now know him to be. Play Misty For Me is a stalker horror film that very much plays to Clint’s star image (ego) at the time as a radio disc jockey whose raw sex appeal turns his fan Evelyn (the great Jessica Walter of Arrested Development fame) into a murder crazy lunatic. Play Misty For Me is immediately confident off the bat, with an extremely laid back style behind the camera, almost too laid back to make this thriller particularly thrilling but it does lend the film a unique rhythm and charm. The most amusing moment is when Clint’s Dave attends the local jazz festival. The story stops dead for about 5-6 minutes and the shooting style morphs into a mini concert film. That’s certainly one way to get the studio to fund your excursion!

23. Sully (2016)

Based on the incredible true story of the ‘Miracle on the Hudson’ where Captain ‘Sully’ Sullenberger (played by Tom Hanks) landed a plane onto the Hudson River after a malfunction, saving the lives of all 155 passengers onboard. Sully is arguably Eastwood at his most utilitarian, a straight down the middle procedural without an ounce of fat on its bones, taking a fairly short event and re-litigate it over and over across it’s 90 minute runtime without it ever feeling repetitive or stale. A classic Eastwoodian examination of what makes a hero, and the effects of mythologizing such people.

22. Sudden Impact (1983)

Dirty Harry and The Man with No Name (from the Leone westerns) are the two pillars of the Eastwood persona, his two most defining roles. Sudden Impact, the fourth entry in the Dirty Harry series sees Clint step in as director for once, delivering the best of the four sequels. This entry is most notable for the “go ahead, make my day” catchphrase. Arguably the darkest entry after the original, Sudden Impact takes on a duelling narrative with Harry pitted against a female vigilante (Sondra Locke) going after the gang that brutalized her and her sister a decade ago. She, like Harry takes the law into her own hands when the justice system fails, making her a sympathetic foil and mirror to Harry. Only difference is one has a badge, and one doesn’t, which makes all the difference and no difference in this film.

21. Cry Macho (2021)

After making 3-4 “final” screen performances in the past decade, Cry Macho seemingly is the last hurrah for Clint, the movie star. Clint stars as Mike Milo, a former rodeo star who gets tasked with going to Mexico to retrieve his boss’ son and bring him back stateside. The first question most viewers will ask is why a then 91 year old is sent for such a job and that’s the secret to unlocking its particular charms, he’s not sending a 91 year old…he’s sending the image, the persona that is Clint Eastwood. Divorced from context, it’s a fairly implausible, often clunkily written drama with uneven supporting performances and a lack of thrill as a thriller. One cannot approach the film this way, all of its power and subtext comes from the fact that you’re watching Clint Eastwood at this advanced age and all that entails in relation to his past work. Where his other “final” films like Gran Torino or The Mule carried with them a sense of regret and retribution, a man at the end of the road burdened with guilt looking to make up for his mistakes, Cry Macho is eminently laid back and serene. After burdening that guilt, he’s moved on and at peace with himself. At this age, every moment is a blessing, so you cherish the small, beautiful moments in life while imparting some wisdom to the next generation when you can. The film is ultimately at its best during its plotless second half where Clint and the boy simply enjoy life in this small town, helping animals, taking naps, and dancing with pretty ladies. A beautiful film.

20. True Crime (1999)

Speed zoo!

True Crime is another classic Eastwood thriller that follows Clint as Steve Everett, a washed up news reporter tasked with covering the upcoming execution of a death row prisoner (brilliantly played by Isaiah Washington) at midnight that same day. While doing the basic coverage, Everett starts to realize that the prisoner may in fact be innocent. Racing against the clock and the confines of these institutional powers, Everett’s journalistic passion starts to burn again as he works to figure out the truth behind this story. Clint’s unassuming procedural like camerawork emphasizes the dehumanization inherent to these processes. While notable for it’s sobering and unfortunately still timely examination of the cruelty and discrimination in the US prison system, True Crime is also surprisingly very funny especially since the film has James Woods, Dennis Leary and Clint bantering with one another. Yet the humour and cynicism never undermine the emotional stakes.

19. Changeling (2008)

A true story that is so overwhelmingly heartbreaking, ridiculous, maddening, and frustrating that you’ll be convinced this film made it all up for dramatic license…it does not. Set in the 1920s, Changeling follows Christine Collins (Angelina Jolie) a mother whose son goes missing and is found by the police months later. Initially overjoyed, Christine starts to realize that the boy who was “found” is not her child. To cover up their mistake, the police captain has her committed to a mental asylum. One of the most incisive depictions of the patriarchal systems and oppressive nature of the institutions America is founded on, one that would rather punish and demean an innocent woman than admit to it’s shortcomings. An understandably tough watch, Changeling is emotionally draining and incredibly powerful with Jolie giving a career best performance.

18. The 15:17 to Paris (2017)

I know what you’re thinking, and yes that 15:17 to Paris but…hear me out. Like many (the vast majority), I did not like this film when it came out, but I could not deny just how fascinatingly bizarre this whole project was, from inception to execution. This has to be one of if not THE strangest major studio release of the past decade. Based on the true life story of the thwarted terrorist attack on the titular train prevented by 3 Americans while on vacation in Europe. Unlike other true story adaptations, Clint cast the real guys to play themselves, three non-actors, and not just them but the other passengers on the train too! The 15:17 To Paris is another late era work preoccupied with the idea and mythology surrounding heroism, with this film being the most extreme example in deconstructing such images.

You may be wondering how one makes a film about the three Americans who stopped a terrorist attack on a train (an event lasting mere minutes) into a feature length story and well…you don’t. The attack sequence in the film’s climax is as thrilling and visceral as you’d want (if Eastwood had “lost it” as many claimed, this finale would not be as it is) while the preceding hour and a bit is a whole lot of nothing! And that’s the point, real life is boring, not a movie. In casting the real life people to play themselves (who can’t act), you inherently remove any gravitas that an actor’s performance would imprint onto the role (consciously or not). Eastwood’s lack of style and matter of factness does wonders in portraying the mundane reality of these men’s lives. They never have anything particularly insightful or interesting to say, they fail and screw up and say/do dumb stuff as anyone would from time to time. They’re completely normal individuals who happened to be in the right place, at the right time and did the right thing. I’d struggle recommending this one to most viewers but it’s an essential late Eastwood text as fascinating as it is head scratchingly bizarre. This one’s for the real Clint auteurists.

17. Pale Rider (1985)

The B side to High Plains Drifter, Pale Rider is another supernatural tinged western with Clint embodying the angel of death who rides atop a pale horse who finds himself protecting a small town from greedy prospectors. Probably the most traditional western he’s directed, lacking the overt revisionist angles of Drifter or Unforgiven in favour of a more straight forward structure. Pale Rider delivers gorgeous, sweeping mountainous vistas, evocative gunfights, and a surprising amount of heart at the centre of it.

16. Million Dollar Baby (2004)

Million Dollar Baby won Clint his second Directing (and Best Picture) Oscar. What begins as a spin on that Rocky underdog story evolves into something unique, elevating the entire narrative into one of Eastwood’s most powerful and heartbreaking films. Million Dollar Baby follows Hillary Swank as an amateur boxer, hoping to be trained by Clint, a grumpy cynic who refuses to train her. Eventually through seeing her determination (and after a nudge from his close friend played by Morgan Freeman), he decides to show her the ropes. Over time, we see the two bond and he becomes a surrogate father to her through thick and thin. Clint’s role is another variation of his late career archetype, a man who neglected his own family in lieu of his work, striving to make up for that now. He sees Swank as a second chance at life, both professionally and personally. Due to its heavy nature, it’s not one I revisit often but it leaves a hell of an impact.

15. Absolute Power (1997)

Easily my favourite of Clint’s paperback novel thriller films. Absolute Power follows Luther Whitney (Eastwood), a master thief who, in the course of robbing a home, witnesses a murder in which the President may be involved. Now on the run with every 3 letter agency on his tail, Whitney has to decide between protecting himself or upholding justice. Absolute Power is a deliriously silly potboiler that’s directed with style and housing a killer supporting case from Gene Hackman to Ed Harris. What really elevates this one for me is the central relationship between Clint and his estranged daughter (a recurring theme) whose work kept him away from home during her childhood. This meta, self reflective element blossoms into a slight yet beautiful gesture as to the ways an artist can connect to people through their art, while a film, drawing, painting can never heal a wound, something beautiful can come of that pain all the same.

 

14. White Hunter, Black Heart (1990)

White Hunter, Black Heart marks a real turning point for Clint’s career. His onscreen persona was cultivated through the macho tough guy image (which he excels at to be fair) and he’s spent the latter half of his career subverting that image. Prior to this, with films such as Bronco Billy and Honkytonk Man, he had gone against type playing characters that audiences hadn’t seen from him but White Hunter, Black Heart is when he goes into full deconstruction mode. Based on the book that’s a thinly veiled account of the making of John Huston’s The African Queen, Clint plays larger than life film director, John Wilson who sets off to Africa to make his next picture. But that’s an afterthought for him, for he wishes to hunt down an elephant above all else. White Hunter, Black Heart is a bleak showcase of masculinity, egotism and the destructive nature they incur, tying it all up into a critique on colonialism. It’s no surprise something this different (for Clint) and dark bombed at the box office, but it’s one of his most underrated efforts.

13. Juror No. 2 (2024)

 

In Clint We Trust! Even as one who champions Eastwood’s quirkier late style works, I always had to recommend them with an asterisk. That could not be further from the truth with his latest, a completely, overwhelmingly normal film, with a brilliant script and not an ounce of fat on its bones. Juror No. 2 follows soon to be family man Justin Kemp (Nicholas Hoult) who when called in for jury duty on an upcoming murder trial, starts to realize that he may have been the one who did it. Grappling with the guilt and circumstances, Kemp now must find a way to sway the jury to free the accused and ensure he’s not found out. It is genuinely astonishing how much Clint at 94 really locked in for this one, pure classical filmmaking the likes of which we do not see anymore. From front to back, I was just stunned, sitting in silence for a few minutes as the credits rolled and my friends discussed it around me, taking it all in.

The third act is a masterclass in tension and mounting uneasiness, I felt a pit in my stomach grow the further it went along, and that ending? Wow. Less a straight courtroom drama than a morality play, what is truly impressive is how much it lets the audience sit with these ideas for themselves, there’s no guiding hand or moralizing, nor does the film provide you with that exhalation of relief which works to great effect. Despite his age, Eastwood remains one of the most important contemporary filmmakers working today, tackling American institutions for what they represent in modern society and shining a light on the everyday realities and locations not reflected on screen. While Clint is no radical, Juror No. 2 does continue his streak of observing (quite damningly I’d add) the flawed institutions which we base our ideals of society off. To what lengths will people go to compartmentalize the blurring of truth and justice for the sake of personal convenience and not “rocking the boat”?

12. High Plains Drifter (1973)

Clint comes out of the gate nearly fully formed by his 2nd feature, High Plains Drifter, a film that follows an unnamed supernatural cowboy (Eastwood) who is hired by the town mining company to protect them against three bandits coming their way. However, this job Clint takes on may be more personally motivated than he lets on. This revisionist spin on his spaghetti western image is pushed to its most evil and shocking extreme, as its vision of the Wild West is as surreal as it is nightmarish. There are no innocents or heroes riding off into the sunset to be found, only death.

11. Honkytonk Man (1982)

Set during the Great Depression, Honkytonk Man follows Red Stovall (Eastwood) as a struggling country singer with tuberculosis, who after getting invited to audition at the Grand Osprey, a nationally syndicated radio country showcase, decides to go out on a road trip across country with his nephew Whit (Kyle Eastwood), seeing it as his last chance to be somebody. What starts as a fun, laid back road trip dramedy slowly morphs into a real tearjerker by the end. Clint brings in a vulnerability and mortality to the role, something unseen in his evolving screen persona up until now, with a third act static close up capturing an expression so haunting and sad from him that it makes me tear up.

10. Hereafter (2010)

Wherein Eastwood makes a triptych “arthouse” film on the afterlife and reconciliation of death. Hereafter is a semi-fantasy drama that follows three separate plotlines all connected in some ways by death. While such a spiritual/fantastical premise seems so outside of Eastwood’s wheelhouse, it’s his approach that fits right in alongside any of his other films. Presenting the mystical and supernatural elements in such a literal matter of fact way that doesn’t so much explain the afterlife as use it as a framework to examining 3 lonely people across different classes and countries. The film has no narrative, opting for a slice of life approach to the three main narratives. George (Matt Damon) is a middle class American psychic who is burdened with a gift or curse to speak to the dead. Marie (Cécile de France) is an upper class French news reporter who survives a near death experience in the midst of a tsunami. Marcus (Frankie McLaren/George McLaren) is a lower class English boy reeling from the death of his twin brother. Eastwood avoids the grand scale and fantastical elements that play a part in the story, he is above all a deeply humanistic filmmaker and grounds the film in the inherent sadness and longing of each character. Hereafter certainly won’t be for everyone but it’s one of his most unique and moving pictures. Filmmaker Ryusuke Hamaguchi (Drive My Car) has listed Hereafter as one of his favourites, and some moments feel like they could’ve come from a Hamaguchi film, so if you’re a fan, might be worth checking out!

9. Richard Jewell (2019)

Based on the true story of the Atlanta Olympics bombing in the 1990s, Richard Jewell follows the titular security guard, who discovered the bomb and saved lives, but was then falsely accused of being the bomber by the media and FBI. Another entry in Clint’s late career exploration of real life heroism, the film is a heartbreaking look at when these institutions that have been drilled into our brains as righteous and good are turned against you. If you are perceived as somewhat outside of their “norm”, our institutions will crush and dehumanize you without a second thought. While I’d never call Clint a progressive, his libertarianism does often lead him (intentionally or not) to identifying the root causes of society’s ills. The naivety of Jewell (played brilliantly by Paul Walter Hauser) is ultimately the tragedy here, a man who did the right thing and despite all the abuse and slander, still can’t let go of his preconceptions which only bury him further, worshipping the same law enforcement looking to nail him. Paired with a terrific supporting cast including Kathy Bates as his mother Bobi, Sam Rockwell as his feisty lawyer Watson Bryant, and Jon Hamm chewing the scenery as Tom Shaw, a scummy FBI agent, Richard Jewell is one of Eastwood’s best and yes, another tearjerker.

8. Letters from Iwo Jima (2006)

The second half of Clint’s World War II duology on the battle of Iwo Jima (following Flags of Our Fathers), Letters from Iwo Jima tells the story from the perspective of the Japanese army, and is filmed entirely in Japanese. While this does make a great companion piece to the first film, both are entirely standalone experiences that don’t require knowledge of either film, so if you can only make time for one, watch Iwo Jima. Shot on less than a 1/10 of the budget of Flags, this is a much more personal affair, foregoing the large scale war battle spectacle in favour of intimate drama. The film primarily follows General Tadamichi Kuribayashi (Ken Watanabe) as he and his men prep for the incoming US attack, a battle most know will be a futile mission. It’s rare for American war films, especially in 2006 to be from the perspective of the other side, and Eastwood avoids any potential propagandizing efforts, treating the story and characters as respectfully as he did for their American counterparts in Flags. On both sides are soldiers ripped from their families in pursuit of what they believe to be right.

7. Gran Torino (2008)

Originally conceived as his retirement from acting, Gran Torino is another meta reflective work from Clint, examining his legacy and him as an icon. If Unforgiven is the final deconstruction of his cowboy persona, Gran Torino is the final word on the Dirty Harry persona. Gran Torino follows Walt Kowalski (Eastwood), a perpetually cranky and racist war veteran who recently lost his wife and now has new set of minority neighbours to contend with. The comical plethora of slurs Walt unleashes throughout this film is extreme in how unvarnished a depiction of racism it is, but this is a film about how that hatred eats away at your soul and alienates yourself from others. That hatred, acting as a coping mechanism for the horrors Walt experienced in Korea, and feeling lost in a changing cultural landscape, a changing America. It’s an accurate look at what a lifetime emulating that Harry-esque persona leads you, lonely bitterness. Masculinity as a tool and curse, redemption and acceptance of man’s actions and violence. These are all themes that have percolated over Eastwood’s long career and continue to be developed across his body of work. I’m glad he’s still acting but if this was his final film as intended, it would’ve been an appropriate capstone.

6. The Mule (2018)

A decade after “retiring” from acting after Gran Torino, Clint returns to the big screen with The Mule. While the former felt like more of a reflection on Eastwood as an icon, this film reads more so as a reflection of Eastwood, the man. Loosely based on the true story of the 90 year old drug runner who became the most successful drug mule in cartel history. Eastwood seems to have taken the premise and imbued his own personal life experience into it in this part road trip comedy, and part reflective melodrama. For much of the runtime, it’s a lighter road film as Earl Stone (Eastwood) drives around in his truck, singing to country tunes, eating pulled pork sandwiches, and still being sexually active at 88. But after a lifetime of avoiding his responsibilities at home to keep having fun on the road, came at a price as Earl attempts to atone for his past mistakes. At his advanced age, time is a luxury that one cannot buy more of, and he’s now coming to terms with that. Clint has played numerous roles at this point of the father whose estranged from his family due to their being pre-occupied by work but it’s never been more touching than in The Mule, an inherent byproduct of the added legacy attached to his age here.

Outside of the meta reflective nature is another examination of American society, one where work is an identity in and of itself and progress is measured by counts on a spreadsheet to determine the value of oneself. The mirroring scenes between the DEA and drug cartel employees facing heat for missing their quotas drive home that point. Earl’s success as a drug mule is tied to his identity, as much as the film plays comedically with his occasional un-politically correct comments, it also contains a particularly harrowing scene where the DEA pull over a Hispanic driver whose vehicle matches the description of Earl’s truck. The hard cut from the Hispanic guy shaking in fear and acknowledging how dangerous it is to be pulled over by the police to Clint singing along in his car as he drives right by the scene says it all really. The Mule has all the thematic meat and social commentary you’d want from a late era Eastwood while also being the funniest film he’s ever made, it’s got it all, a real delight!

5. A Perfect World (1993)

A Perfect World is a film of two halves. The A plot follows Butch Haynes (Kevin Costner), an escaped convict on the run who takes a young boy as his hostage and along the way forms a friendship with the child. The B plot follows Clint as Red Garnett, a Texas sheriff in pursuit of the criminal, with Laura Dern as a rookie criminologist to help with the chase. On paper, A Perfect World is nothing you haven’t seen before but the execution behind and in front of the camera and strength of the writing pushes it into another stratosphere. Under lesser hands, this film’s sharp tonal shifts and gestures towards emotion may ring hollow but A Perfect World is one of Eastwood’s most heartfelt works. The A plot is so engaging that it may be the only time where I get annoyed when we have to cut back to Clint’s sheriff character, but this contrast is necessary to tackle the Eastwoodian themes on masculinity, the messy arbitrary divide between law and lawlessness, and the generational impact of violence. A Perfect World had the unfortunate luck of being sandwiched between two of Eastwood’s most acclaimed films, leading to it becoming fairly underseen as a result, but I would strongly urge seeking it out, Clint’s 90s run is legendary.

4. The Outlaw Josey Wales (1976)

After Josey Wales’ (Eastwood) wife and son are brutally murdered by Union soldiers, Josey takes up the pistol and goes down a road of vengeance, joining a band of Confederate rebels roaming the countryside. After his group is betrayed and killed, he becomes an outlaw on the run and along the way, forms a makeshift family on this journey of revenge. If High Plains Drifter is Eastwood’s deconstruction of the spaghetti western archetype, The Outlaw Josey Wales is his take on a John Ford western. A man of violence fuelled by vengeance slowly regaining his humanity as he puts back together the family he originally lost. The film’s structure and tone mirroring Wales’ character arc, what begins as a down and dirty violent western morph into a more tender tale of unity and redemption with cool cowboy moments notwithstanding.

3. Bronco Billy (1980)

Clint has been quoted as saying “if, as a film director, I ever wanted to say something, you’ll find it in Bronco Billy.” He’s not kidding, ALL of his themes, and preoccupations are found here at their most distilled form. Bronco Billy follows the titular cowboy performer and his Wild West show, a travelling circus that rarely fills seats and is extremely hokey, but Billy and co. put their heart and soul into it regardless. Along the way they find a new assistant (Sondra Locke), a believed to be dead millionaire heir to her family’s fortune, a cold, cynic who slowly finds kinship with the rest of the gang of outcasts as the film goes along. Light on plot or incident, the film opts for a more hang out episodic structure, focusing more on the characters (and moments of slapstick comedy) as we see their camaraderie and overcome their struggles along the way.

Arguably his most self-referential work, Billy’s Wild West Show is to him what Malpaso (Clint’s production company) is to Eastwood, Billy’s friends and lovers operating as stand-ins for those in his real life. Eastwood was the last western icon, and the genre inadvertently or not, died alongside him which I think he feels some remorse over. The film acts as a love letter to that classic mythology of the west from a childlike POV, the image that his spaghetti westerns helped shatter. The power of myth and that western iconography is the recurring through line of the film and what the characters aspire to be. The slight sense of melancholy permeating it all is because it really is a false myth, but in Billy’s idealistic worldview we can all be his “lil pardners” and live under the promise of one shared tent (America) welcome to all. An ode to the outcasts and idealists who make up America. Bronco Billy is Eastwood at his most charming, a bubbly and fun little comedy with enough of an emotional/thematic core that makes it one of his most defining statements as a filmmaker.

2. The Bridges of Madison County (1995)

The Bridges of Madison County follows photographer Robert Kincaid (Eastwood) who, while on assignment in a small town, meets housewife Francesca Johnson (Meryl Streep) and embarks on an intense affair that occurs over four days in the 1960s. Overwhelming in it’s beauty and simple gestures, Bridges is a film that sneaks up on you, the attention to detail and little grace notes bubbling up slowly but surely, never realizing just how connected you were to everything until the final moments hit you like a truck and you’re reduced to a blubbering mess. A pure romance film is unique for Eastwood, its simplicity is deceptive, but the emotional maturity underneath only enhances the raw emotional power of the work. An examination of the traditional family unit and the ways in which it makes us suppress our desires and dreams. On any given day, this might be my favourite Eastwood but alas, #1 can’t be anything else but…

1. Unforgiven (1992)

In many ways Unforgiven is the final chapter of the western genre. Eastwood was around in its heyday with TV series like Rawhide and on film, as he ushered in the spaghetti western, the subgenre that helped advance the death of the classic western with its grey morality and increased violence that de-romanticized the classic west, while creating their own myths. Throughout the three prior westerns that he directed, Clint has worked to deconstruct and dismantle the myth of the western and with Unforgiven, he’s gotten to its core and laid it to rest. Unforgiven follows William Munny (Eastwood), a retired gunslinger who now finds himself a widower with two children on a pig farm until he’s brought back into the fold for one more job, to kill two cowboys who brutalized a prostitute. Bringing along his former partner Ned Logan (Morgan Freeman), Munny clashes against the local corrupt sheriff, Little Bill Daggett (Gene Hackman), and a litany of “western tropes” taken to their realistic, ugly end. Ostensibly a film on mythology and the destructive nature of it, its wild west is a cruel, bleak cycle of violence whose self-induced mythology on cowboys (through tale and fiction) passes down this curse to the next generation. Through the myth of the cowboy, the western genre has shaped the views on masculinity, views on the country’s history and the merits of heroism. “When the legend becomes fact, print the legend” is the iconic thesis line from John Ford’s The Man Who Shot Liberty Valance but it applies to Unforgiven just as much. Clint Eastwood’s magnum opus.

Thanks for reading, and I hope this helped to shine a light on some works you may not heard of you to and/or inspired you to check out some of Eastwood’s lesser known and lesser loved films. Eastwood’s latest Juror No. 2 is now streaming on Max (in the U.S.) and Crave (in Canada), and is also available to rent on VOD. Enjoy!

still courtesy of Warner Bros. Pictures


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