Though he became a well-regarded director starting in the 1970s, and a movie star around the middle of the 1960s,Clint Eastwood’s earliest years in the entertainment industry were on television. His 1950s films generally saw him in smaller roles, so it was the seriesRawhidethat made Eastwood a big name. He had a starring role in the Western show, which began airing in 1959 and ended in 1965, airing 200+ episodes in total.
As such, it wasn’t really until the middle of the 1960s that Clint Eastwood jumped back into the world of film, and he hasn’t really looked back since, with his final film –Juror No. 2–set for a 2024 release, which will mark 60 years since he really became a movie star.He was in eight movies that were released in the 1960s (specifically, between 1964 and 1969), and a decent number – though not all – were Westerns. Those eight films are ranked below, starting with the not-so-good and ending with the great.
8’Paint Your Wagon' (1969)
Director: Joshua Logan
This one’s honestly kind of a disaster, but in a waythat might also be a little funny.Paint Your Wagonis bloated and overlong, and sometimes boring, admittedly. There is fun and amusement to be had in bursts, but also a lot of tedium and pain, to the point where maybe the “t” could be taken out of the film’s title.
What it boils down to istwo men having various misadventures in Old West times while sharing a wife, and occasionally taking part in musical numbers.Yes,Paint Your Wagonis inexplicably a musical, and not a very good one either. Though, for what it’s worth, you do get to see Clint Eastwood sing a song about talking to trees, which could be either a highlight or a low-light, depending on what you want out of a movie like this.
Paint Your Wagon
Rent on Apple TV
7’Coogan’s Bluff' (1968)
Director: Don Siegel
FromPaint Your Wagon, there’s nowhere to go but up, as far as Clint Eastwood’s 1960s releases go. As such,Coogan’s Blufflooks almost good in comparison, but it’s still got some serious flaws when put up against those 1960s films of Eastwood’s that aren’tPaint Your Wagon. It marked the first time Eastwood collaborated with directorDon Siegel, with their other four films all being improvements.
Coogan’s Bluff gave Eastwooda chance to be cool in a non-Western, and he seized the opportunity with a small amount of success, here playing a Western-type character – a deputy sheriff – out of his element with a job that takes him to New York City. Call it a warm-up forDirty Harryif you want, which came out two years later and also involved Eastwood and Siegel.Coogan’s Bluffhas its moments and a solid enough premise, butnot much by way of story to sustain a level of excitement for a feature-length runtime.
Watch on Amazon
6’The Witches' (1967)
Directors: Mauro Bolognini, Pier Paolo Pasolini, Vittorio De Sica, Luchino Visconti, Franco Rossi
The role Clint Eastwood played in the spaghetti Western genre is well-established, butwhat’s less well-known is the fact that he also had a role in another Italian production from 1967 calledThe Witches. To be fair, he is only in one part ofThe Witches, given it’s an anthology film (thoughit’s not as fantastical/supernatural as you might expect), but is prominently featured within that one segment; the last of the whole film.
Eastwood’s dialogue is dubbed into Italian, and he plays a husband who’s become more boring as the years have gone on, frustrating his wife and driving her to escape into fantasy increasingly often. It’s a bizarre and entirely uncharacteristic role for Eastwood, but the novelty of seeing him in a film like this makes it kind of worthwhile. Elsewhere, the other segments are certainly hit or miss, butPier Paolo Pasolini’s contribution, which is the third overall, does also prove interesting and absurdly funny.
5’Hang ‘em High’ (1968)
Director: Ted Post
Hang ’em Highis a more than solid Clint Eastwood Western, even if it falls a little shy ofthe man’s best work as an actor. It revolves around a Marshall swearing revenge on the people who tried to hang him but mistakenly left him for dead without the job being done properly.He, on the other hand, has no intention of leaving any job only half-done.
It is, sadly, a little plodding when it comes to pacing, withHang ‘em Highgetting off to a good start, though slowing down a little more than it perhaps should’ve as time goes on. Things wrap up well enough, and Eastwood’s reliably good as he tends to be, but it’s probably not a must-watch for anyone who isn’t a fan of the actor. Those who are, though, will probably get a little something out of watching this one.
Hang ‘Em High
Watch on Tubi
4’Where Eagles Dare’ (1968)
Director: Brian G. Hutton
AlongsideCoogan’s Bluff,Where Eagles Darewas another significant Clint Eastwood movie thatdemonstrated the actor’s desire to move away from Westerns, and arguably stands as his first great non-Western. Instead of that genre,Where Eagles Dareisa war/action/adventure movie, set during World War II and revolving around a dangerous mission that involves rescuing an American general from a seemingly impenetrable fortress.
In a sense,Where Eagles Darescratches the same itch as some other 1960s World War II movies that areset up almost like heist movies, being comparable to other “dangerous mission” films likeThe Guns of NavaroneandThe Dirty Dozen. That following of a formula might mean thatWhere Eagles Darelacks narrative surprises, but such things don’t matter when there’s tension, excitement, and action sequences that more than compensate.
Where Eagles Dare
3’A Fistful of Dollars’ (1964)
Director: Sergio Leone
This is where the fun begins. Clint Eastwood’s rise to fame will always belinked withSergio Leone, with both making names for themselves thanks toA Fistful of Dollars. Honestly, the film can also be admired for helping make spaghetti Westerns a thing, with this film being produced in Europe and having a cast filled with Italian actors, excluding Eastwood himself, of course.
The narrative here concerns the Man with No Name rocking up in a town that’s been impacted by a gang war, so he begins trying to manipulate both sides into taking each other out, swooping in and taking out any stragglers himself after.It’s a fun idea for a movie that wasessentially stolen from an Akira Kurosawa movie, but it still holds up and laidthe groundwork for even bigger and better things, as far as the filmographies of both Eastwood and Leone go.
A Fistful of Dollars
2’For a Few Dollars More’ (1965)
An example ofa follow-up movie that’s betterin just about every way,For a Few Dollars Morewas the movie that got to run becauseA Fistful of Dollarswalked. It sees Eastwood once more playing the Man with No Name, here getting wrapped up in another violent Western adventure alongside a bounty hunter played byLee Van Cleef, who ultimately gets more to do character-wise and narratively.
This is as a result of Van Cleef’s character pursuing a target for personal reasons, and the Man with No Name being after him for the money, leading to an uneasy and entertaining alliance forming between the two.For a Few Dollars Moreisa little more epic in scope thanA Fistful of Dollars, but it also has a more engaging and emotional storyline at its core, overall becomingone of the all-time great spaghetti Westerns, as a result.
For a Few Dollars More
The trilogy of movies with the Man with No Name at its core peaked in 1966, though, thanks to the release of the legendaryThe Good, the Bad and the Ugly. Put simply, this is a Western that’sjust about as perfect as Westerns can get, with a simple plot that centers on three men competing to find a stash of buried gold somewhere in the desert, all while the American Civil War wages around them.
Lee Van Cleef returns, but as a different character, though it’sEli Wallach’s Tuco who ends up stealing much of the film, as well asgetting many of its best lines.The Good, the Bad and the Uglyjust works in every way it needs to and holds up immensely well all these decades on from its release.Its influence can’t be understated,and it’s quite comfortably the best 1960s movie Eastwood starred in, if not the best movie he’s ever been in, regardless of genre and decade.
