Wow... This one is gonna be tough as hell... So many choices and so much consistent good work.
1. Dirty Harry: Maybe the best of the down and dirty, no pun, films about the fears of urban decay from the 1970's this film is way more than it is on first glance. Yes, it's the grandaddy of the "cop on the edge" type crime films. Yes, it's a reactionary piece, with big appeal to a certain type of American film goer that fantasizes about the use of violence to clean the streets of undesirables (that terms having a particular connotation for some...) and it's in line with other such films that came later like Death Wish, obviously a rip off of Dirty Harry with a more exploitation angle. But this is a really well made film as compared to those clones that came after. Perhaps it's the result of it's origin as a studio film that was originally supposed to star Frank Sinatra. The director, Don Siegel, gives the film a real sense of time and place, which arguably, is what makes it timeless. Working with Eastwood the film doesn't pull many punches with it's conceit, and despite the main character becoming a franchise headliner the truth is this film probably should be viewed as a stand alone film with definitive ending. Harry Callahan is blunt, obsessive, prone to violence and with little sympathy, but the film tells us he's what's needed in the urban jungles of a crumbling America of the time. You can quibble about those aspects, I sure think it's as said a reactionary piece, but it's a really well done one that grabs you. Andrew Robinson is incredibly well cast as the villain and he's easy to hate. Which is maybe the point of the film, as a release valve for many to focus their emotions about the then rising crime and unraveling of the social order apparent in the news everyday. Regardless, the film still works even outside that context. I'll never forget watching it with one of my cousins in the 1990's. He had to have been about 13 or fourteen. I was already in my early 20's and wanted to share this with him. He was a little standoffish towards the film at first but he got so into it he was on his feet when Harry appears on that overpass in the third act. Eastwood marshalls his stoic charisma to it's fullest in this movie, imbuing every sneer and squint with a withering contempt that you as a viewer are totally in support of. More than even his Westerns I think this is the film that solidified Eastwood's appeal and delinated his on screen persona for decades to come. A true classic in every sense.
2. Unforgiven: Clint gives us the best and most amazing breakdown/deconstruction of the Western in this film he also directed. Eastwood was at the forefront of re-energizing the Western and re-imagining it early in his career away from the simple ingratiating tales that were the hallmark of the previous giant of the genre, John Wayne's films. Eastwood's Westerns were a dirtier and dingier affair, much more likely to show the scuzzy underbelly of human nature. Still, he reached new heights with this film about the truth of the cheapness of life and death in a frontier world where everyone is armed and the difference between what is lawful and what's just might makes right is as blurry as an old man's eyesight. Clint brings his incredibly long lived experience as a star and director of Westerns in their late stage to deliver a tale that matter of factly upends the usual expectations of a Western revenge story. The cast he collects for this film is impeccable, filled with talent to spare, even in small roles. For any other mortal this film would be a crowning achievement to end a career with but Clint continued on still delivering well after.
3. Kelly's Heroes: Does any other film of Clint's do more to please every possible segment of the audience than this hybrid war film? It's obviously a WWII action story but it's also a heist film BUT it's also a dark comedy, and it's pulling influences from Clint's westerns... It's got it all. Underdogs you are rooting for, broad AND adult humor, well crafted and memorable characters and truly impressive production values up there with any of the great WWII films. Now, I do think it's true that Clint in this film takes a back seat to the rest of the ensemble, but he's still a driving force both in front of and behind the screen. What he managed to pull off is really magical and you can see this movie's influence on a wide array of film makers not least of which is the work of Quentin Tarantino and his multi-layered, mulit cast epics. And what a cast this film has. Telly Savalas doing what he does best as a no nonsense soldier with a crusty, greasy charm. Donald Sutherland as the anachronistic proto-burnout in charge of a deadly team of tankers. Carol Oconnor as a pseudo Patton... Well I could go on given how big the film's cast is. Needless to say I love this movie as a great action film that delivers the right kind of comedy with a colorful cast of characters you can't ever forget, all in a movie that's tight all around, from production values to script. I personally think this could be Clint's most outright enjoyable film.
4. The Dollars Trilogy: Okay... Maybe this is cheating but these films are so influential and so different to most of the Westerns that came before them that putting them all together makes sense to me. It's a sprawling and sometimes even strange journey of a Western series that's sort of not even a series. But does it ever deliver on compelling movie making. Director Leone is a wizard bringing together all these separate elements that combined make for a fever dream of an almost fantasy old west. Clint's trajectory was forever changed when he agreed to star in the first film, A FISTFULL OF DOLLARS, a remake of the Kurosawa film YOJIMBO. Gritty and dirty, it follows the contours of the original pretty closely while adding it's own flavor. The sequel, FOR A FEW DOLLARS MORE finds it's own voice by placing it in the world of old west bounty hunters and teaming Clint with Van Cleef. Finally the crowning glory of THE GOOD, THE BAD, AND THE UGLY, with a reteaming with Van Cleef as a different character and Eli Wallach as the deplorable comic relief in a movie that operates like a symphony or quasi opera, no doubt owing to the amazing work of Ennio Morricone's score. It cannot be underestimated what this film did for the Western, which even in the hands of it's then masters like Ford, still had a very staid and formulaic presentation on screen. Not so here. Clint does his part to differentiate his "Man with no name" from the icons that came before him to the point that I think it's fair to say until this day his persona now is what people think of when the mythical "cowboy" comes to mind. Eastwood made the best decision of his life linking up with Leone and you can see that he was more than just hired talent but absorbed as much as he could about directing from the Italian film legend as he would show in his mid and late 70's output. Influential, engaging, artistic and visceral... The Dollars Trilogy stands the test of time.
5. Heartbreak Ridge: I just love this movie and I honestly don't know how it ranks in most critics' or fans' estimation as compared to the rest of Clint's output. All I know is it's a hell of a character piece and a damned fine film about the Marine Corps. Cline directs himself as a tough as nails veteran Marine Gunnery Sgt. that is probably too old for the 1980's world he's in but who is determined to keep marching until he drops. Clint's Sgt. Highway is like many of the characters he has played but I think it's this film where Cline, unlike a lot of other stars known for action films, started to reckon with age, and it's a part of this film all the way through. The movie is also, frankly, filled with lots of cliche's but that's okay because Eastwood executes them all to their utmost, so while we've all seen the rag tag band of neer'do wells bond to become a unit before that doesn't make the journey we take with Highway's platoon of Marine Force Recon Corpsmen any less entertaining. One of the thing for the most part when it came to Clint's 70's and 80's output was that he was making dramatic films with strong action elements in them rather than pure action films. Here is no exception where an entertaining character study with strong dramatic overtones is also able to deliver on grounded action in it's third act. Put this film on and I dare you not to be drawn in until the end. Everything is on point and if you haven't seen it I suggest giving it a whirl.
6. Two Mules For Sister Sara: I like to think of this film as Clint's most sardonic of his Westerns and you can see that it's of the same type of film as Kelly's Heroes, where it plays with the conventions of the genre. It's a bit of a trifle actually, but it's just so enjoyable and the on screen chemistry between Eastwood and co-star Shirley MacLaine is more than enough to drive the movie. If anyone has ever seen the trailer for the film it's hilarious because it's not at all what the trailer describes. It's a low key western really even if it takes place in tumultuous time in Mexican history. Still it's got laughs and tension and it's two leads work off one another really well. On a personal note, as a ten year veteran of a Catholic education can I say... Man, I wish there were more nuns like THAT.
7. High Plains Drifter: Drawing from Leone and Siegel, Clint again directs himself in another yarn that revels in the scuzzy nature of the the old west. And man, is this film ever scuzzy. There's far too few innocents in this film and that's kind of the point. The whole film plays out like something that might have been read in a Weird Western Tales comic or the Twilight Zone. There's also a bit of Kurosawa in the film too. Eastwood knows how to take his influences though and make something uniquely his own and this film is probably not something that Leone, Siegel or Kurosawa would make. A story where essentially a whole town pays for it's sins along with the criminals that terrorize it, this is another Eastwood western that probably wouldn't have been conceivable at the height of the John Ford/John Wayne era.
8. White Hunter, Black Heart: This is a thinly disguised biopic about the Hollywood director John Huston but it works as it's own film regardless of it's origin. Of all of Clint's films I think this is the one that has the absolute snappiest dialogue and Clint's maybe at his most verbose playing this larger than life director obsessed with taking down a bull elephant, more so than perhaps than actually finishing the movie he's in Africa to produce and direct. As stated, Clint's character has a lot of quick wit and there are some lines for the ages in this. I will say, I will always have to give the film some demerits because while co-star Jeff Fahey isn't bad, he perhaps was just to unseasoned an actor to hold his own on screen with Clint at the time. Still, Clint gets the most bang for his buch as the costuming and sets are truly evocative of the era and Eastwood is never as sauve and stimulating as screen presence than he is in this movie about the movie business and the people that populated it during it's golden age.
9. In The Line Of Fire: Eastwood was perhaps chasing some of Hollywood's trends with this film but still managed to make it his way. Following in a long line of thrillers using the secret service as a hook Clint is a long time veteran of the service who was on JFK's detail the day of the president's assassination. Decades later he finds himself thrown into another murder plot against the current president and the focus of the would be assassin played by John Malkovich, doing what was even then already the cliche of the well spoken and highly intelligent killer who acts as a counter to the more down to earth hero. Like with Heartbreak Ridge, Clint again integrates the issue of age and aging into his character while still managing to pull off a romance with co-star Rene Russo, decades his junior. This aspect is again something that makes Clint stand out in the world of 80's and 90's action heroes and makes his characters that much more real than the supermen that Stallone and Arnold ran around as for so long. All in all it's a very well done film of it's type that Clint makes all the better by his presence and I would be remiss if I didn't mention underrated director Wolfgang Peterson who oversees the proceedings with solid directorial chops.
10. The Bridges Of Madison County: Let's not beat around the bush... This is schmaltzy film. But that's not damning. It's maybe Clint's most "real" film in that it's about down to earth human emotions of the everyday kind. Clint's Robert Kincaid is not the tough guy projection of so many characters he's played but I think perhaps a more than real reflection of Clint the artist, yes indeed, ARTIST, that he is. And as both a co-lead and director Clint brings all his craftsmanship to bear on this small tale of two people making a connection in a short time who have affects on one another throughout their lives. While it's a story that touches the romantic, in more ways than one, in us all it's also real in it's characters and plot and Eastwood and Streep sell you this sweet and bitter meeting of souls. A quiet film that makes you ask yourself all kinds of questions about your life... I can't think of anything that's better to say about the work of a filmmaker and star and in this case it's the product of well known Hollywood tough guy, Clint Eastwood. Who'd a thunk it?
This was so far the HARDEST list for me because the amount of Clint's work is so wide and there's so much good stuff to choose that it was pulling teeth trying to figure out what to put on and what to leave out.
