I’d happily be wrong if Clint Eastwood managed to find the money for one more film after Cry Macho, but I don’t think it’s going to happen. His last two films were box office disappointments, he’s been on the wrong side of the political monoculture of Hollywood for too long, and the man is well into his nineties, creating potential insurance risks. Yeah, I think he’s done.
He’s had quite a career, though. Starting as a bit player in things like Revenge of the Creature, becoming a breakout international star under Sergio Leone, and then parlaying that into a successful Hollywood acting career, especially under Don Seigel, he was catapulted to Hollywood superstardom with Dirty Harry, and he never looked back. He was smart, though, realizing that he could be more than just an actor, and he proved his ability to manage a film set efficiently with Play Misty for Me. He parlayed that into a directing career that lasted more than fifty years, directing forty films, winning two Best Director Oscars, and meeting consistent financial success to just keep going. That he lasted this long is something of a miracle.
He was effectively a studio director in an era without a studio system. He started making films for Universal, but he moved to Warner and mostly remained there for the rest of his career. He took what jobs he wanted, balancing his own personal impulses with the idea that the audience needed to be entertained long enough to build his own cache as an artist and just go in whatever direction he felt like, knowing that an audience would come along with him no matter where he went. It was a strategy that paid off for a very long time.
I don’t think it would be untoward to equate him to John Ford, not because he is known for westerns but because of his attachment to a studio, his efficiency at working, and similar highs and lows.
So, even if he’s done, he provided some great films (and a few not so great ones) as his legacy. Below is the definitive ranking of all forty of his films, and don’t forget to check out the rest of the definitive rankings to bask in their definitiveness.
40. Midnight in the Garden of Good and Evil
“It doesn’t work. It’s a real misfire from Eastwood which would have felt more at home with his uneven 80s output rather than his much more solid 90s output. It’s a misguided effort to translate an inherently uncinematic source material to film.”
“Eastwood doesn’t bring the sense of tension that the film really needs, getting lost in Monument Valley while losing focus of the actual plot.”
38. Breezy
“It’s a weird little film, and I don’t think it works. The stakes are too low, the conflict introduced far too late and too easily overcome, and the ultimate message feels too much like wish fulfillment rather than an actual dramatic development, but Eastwood makes films well and William Holden is solid. I can’t hate it, but it’s definitely not good.”
37. Blood Work
“Meh. It’s not terrible. It’s watchable, but not a whole lot else.”
36. Firefox
“When setting out on this Eastwood adventure, it was Firefox that I was probably most interested in because it felt so completely out of place. Well, considering The Eiger Sanction, it’s not as out of place as I assumed. Eastwood has made worse, that’s for sure, but he’s also made better.”
“I don’t hate the film, but after two viewings I can safely say that it’s one of Eastwood’s films that I find myself least likely revisiting again. There’s simply not enough there to enjoy as a whole, though it does have its charms.”
34. Cry Macho
“Is this the worst way for Clint Eastwood to stop making films? Not really, but it’s far from his best work. It’s nice, unchallenging, and not all that interesting, but it moves efficiently and gives its star one last ride in the saddle.”
33. Pale Rider
“The inelegant intertwining of the two main plots really just creates confusion. It hinders a lot of the film’s enjoyment for me. The final shootout, for instance, is a quality bit of tension based editing and filmmaking in general, but it feels like it comes from a different movie than the one we had started two hours prior. I admire the film in parts, but the dichotomy of the film’s central stories just hampers the entire experience.”
“It has its charms, but it’s a fractured package that doesn’t gel. I did love the outdoor photography a whole lot.”
32. The Gauntlet
“It’s just that there’s not a whole lot to hold interest in between its handful of action scenes. Overall, it’s okay, a lesser work of a director who had already shown that he was capable of more.”
31. Jersey Boys
“It’s a script that simply takes on too much to do anything really effective with it. Still, the first half is actually quite fun.”
30. The Rookie
“Really, though, this was the price Eastwood had to pay to make White Hunter Black Heart, and he approached it quickly and professionally, like he usually did. He didn’t cover himself in glory in making this wannabe Lethal Weapon, but I don’t think he embarrassed himself either. It’s okay.”
29. True Crime
“As a whole, though? The movie’s not really good. The mystery is thin and obvious. The film’s reality around the investigation feels artificial. Frank’s scenes are all mawkish. It’s not an outright failure of a film, there’s too much solid and even entertaining stuff sprinkled throughout, but the whole feels malformed.”
28. Heartbreak Ridge
“It’s not Eastwood’s best effort at all, but it was largely pretty solid for most of its runtime. That ending just doesn’t work with what came before, though. It’s not bad, but it’s just not what the film needed at all.”
27. Bird
“Bird was finely produced and well acted, but it felt too all over the place, trying to gather up as much of the life of Charlie Parker that could fit into 160 minutes. It was really well received upon its release, and its obvious that Eastwood had a lot of love for the subject, but I just wished for greater focus.”
“So, I’m still mixed on the film. I don’t feel the emotional weight of Parker’s death, but I still find the whole journey interesting. A lot of that has to do with Whitaker’s performance, but there’s also something to be said about the physical production that very well captures the look and feel of 1950s New York and Los Angeles.”
26. Space Cowboys
“The first two-thirds of this film is a light, professional, and often very funny tale of old men getting to show the young ‘uns that they still have the right stuff. The last third is over-serious for this kind of movie and doesn’t have the right amount of support from the rest of the film for its requested pathos.”
“I think Eastwood proved what he set out to prove: he could make a movie and he could make it well. I think he may end up being more than just a movie star if he keeps this up.”
24. J. Edgar
“So, I like the film. I think it’s a handsome, well-acted film with DiCaprio serving as a solid foundation on which the film is built”
“And yet, I still think the film is a minor success. Kuribayashi is a very nice character that seems to fit with the history, and Watanabe is a wonderfully gentle soul to bring the man to the screen.”
22. Sudden Impact
“Sudden Impact is barely a Dirty Harry movie, but it’s still a pretty good movie.”
21. Sully
“Still, as a portrait of the lowkey heroism that can come out of nowhere and inspire, Sully is a success.”
“Still, Eastwood proves himself capable of managing a large production like a modern-day war film. He gets good performances from his actors, especially Beach, while bringing his consummate professionalism to the visuals. It just doesn’t hit like it really should. It’s admirable and handsome, but the hints of the kind of emotional connection it could have had, especially through Beach’s performance as Hayes, leave me wanting more.”
19. Tightrope
“It’s pretty good. It could have been great if it had more fully committed to one of its two main approaches to the story, but as it stands, it’s a pretty solid combination of the two.”
18. Hereafter
“He was trying to be European arthouse, and yet I don’t think he has the sensibilities for it. He kind of ends up between cinematic places, and his landing isn’t the most elegant thing in the world. It’s not going to appeal to people with more general tastes because the three stories are so disconnected for so long and the story is so small while the art house crowd is going to see the third act sellout. I think the film works in its own limited way, but I do wish it had fulfilled its promise in the end.”
17. Honkytonk Man
“There are some really nice character moments at play, especially late, but the film ends up playing a bit too generically to become something really special. Still, it’s a quite nice little surprise from Eastwood’s 80s output. It’s not great. It’s far from bad. It’s amusing, sweet, and sometimes even a bit touching.”
16. Invictus
“In the end, it’s all uplifting and nice. It really feels like a fairy tale.”
15. Absolute Power
“It has modest goals, and it achieves those modest goals well enough without too much stumbling along the way. Helped by a solid cast anchored by Eastwood in particular, Absolute Power feels more like a quick ditty between more serious projects than something that Eastwood really sunk his teeth into.”
14. Gran Torino
“Gran Torino is an entertaining film with something real on its mind, but it’s hampered slightly by a more generic approach to its second half and some key performances that don’t work very well.”
13. The Mule
“It does nothing unexpected. It’s borderline paint by numbers in a unique setup, but it has the basic pieces in place to work dramatically. If this had been his last film, I would equate it to Alfred Hitchcock‘s Family Plot: a minor work that touched on things he cared about and a decent way to go out.”
12. Bronco Billy
“Bronco Billy isn’t perfect. It has a handful of subplots that go nowhere, and the bringing together of all the plot threads in the final act is the kind of coincidence that rings hollow. However, the core of the film is so strong, endearing, and sweet that it’s easy to forgive the more mechanical issues. It’s a very nice film, and one that I’m really glad I discovered.”
“Eastwood went from a small thriller to prove himself to the genre that he was most known for, and he kind of took the rug out from it like Sergio Leone liked to do. The lack of real narrative meat on the bones reminds me of Leone’s approach as well, while the filming still feels decidedly Don Siegel-ish. It’s entertaining and unpleasant all at once, and I kind of love it.”
10. A Perfect World
“This is a very good film, a worthy follow up to the rather staggering achievement that was Unforgiven, showing that Eastwood wasn’t done producing quality films and that he was going to keep working at his own pace for as long as he wanted. He wasn’t just a movie star directing movies anymore, he was an artist, and he made a touching little movie to keep himself going.”
“I do think this is something of a lost gem in Eastwood’s career. The ending really adds something to the rest of the picture, and the rest of the picture is quite good on its own. As a portrait of a man of appetites being given an up close portrait of the costs of it all, it ends up quite compelling.”
“If it weren’t for the Mustafa character, I’d place this near the top of Clint Eastwood’s body of work. Other than that, though, this is a really special film.”
7. The Bridges of Madison County
“This is really a wonderful film. A quality script filmed well by Eastwood while he manages his actors to strong performances is a very good combination to build a movie on. Eastwood was on a bit of a tear in the early to mid-1990s, and this just continues it.”
“It’s a story that obviously fits really well in with Eastwood’s later, further cynical look at the agreement between the American people and its government that aligns comfortably with films like Changeling and Sully. It’s a triumph of his late career with only one wrong note. Otherwise, it’s a great film that, maybe, should have been his last.”
“A strong script and strong directing creates a complete picture of a story in The Outlaw Josey Wales. Eastwood gives one of his best performances, showing a surprisingly wounded and unsure central hero, while Chief Dan George really shines as Lone Watie, the almost sarcastic and very knowledgeable Indian companion. There are several standout sequences, all in service to a story that knows exactly where it is going and how to get there. This is the pinnacle of Eastwood’s early directing career.”
4. Mystic River
“This is really a triumph of Eastwood’s career. It takes a great script, pulls out great performances from his actors, and he keeps the action on a slow burn that really plays well into the film’s narrative drive. This is his best film since Unforgiven (though he’d certainly made very good stuff), but it’s also a marked contrast to the rather limp Blood Work. This feels like the start of Eastwood’s late stages in his career, and he handles it exceptionally well.”
3. Changeling
“This period of Eastwood’s career feels very similar to Scorsese’s later period with movies like Shutter Island and The Aviator, period pieces with a lot of money behind them and an obvious effort by studios to marry the more traditional elements of the studio system with auteur directors they could trust to not explode budgets or make complete messes. And, much like Scorsese, this kind of money was where Eastwood ended up making some of his best work.”
“This is one of the triumphs of Eastwood’s career. This is a hard-hitting film that perfectly matches with Eastwood’s directing style. It’s some of the finest acting in an Eastwood movie, all laid on top of a foundation written by Haggis that understands its structure and characters incredibly well.”
1. Unforgiven
“This is the complete package of a film. This is easily Eastwood’s best work as director up to this point in his career. If he had retired after this, I would have understood. It’s hard to imagine topping this.”
David Vining, Author 
*Throws tomato*
Bridges of Madison County that high?
I’d watch the Eiger Sanction TWICE before watching that dog again.
I’m shocked you have Changeling at #3 too.
Now excuse me, I’m going to go love my copy of Firefox some more.
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I felt all the feels!
Fight me!
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I almost feel like I should, rhetorically at least. Understand, I am not dissing your opinions…yet. But I gotta know why you’d rank Changeling over the Outlaw Josey Wales or even White Hunter, Black Heart.
The list is the list but I’d love a few words why each is where it is ranked.
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First, I just go by star ranking. If I give it 4, then I look at all the 4s and rank there. The 3.5s then go next, and so on. Remember, I think these things are kind of stupid, but hot damn if the rankings aren’t the best viewed things on my whole blog year after year. Posts 4-6 so far this year are the rankings of Jean-Pierre Melville, Kobayashi, and Hawks.
Ranking within the star ranking, I pretty much have to just go by gut based on my memories and writing. Bridges is actually near the bottom of the 4 star rankings on purpose. Speaking of Changeling, specifically, I was kind of surprised at how much I connected with the film as it played out, and as I was looking through the 4-star reviews, I just knew that it had to be high up. I mean, I think 1-7 are all 4 star movies, are they that far apart in terms of quality in my eyes? It’s just shades of impressions to a certain point (unless you’re talking Unforgiven, which I just could never see placing lower than #1 its such an achievement).
Regarding the comparison between Changeling and White Hunter, Black Heart, well, I gave Changeling 4 stars and WHBH 3.5 stars.
Again, I think the whole ranking thing is dumb, but hot damn…those clicks.
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