Honorable Mentions: Unforgiven (1992), The Good, the Bad, and the Ugly (1966), The Outlaw Josey Wales (1976), The Rookie (1990), In the Line of Fire (1993)
5. True Crime (1999)
This Eastwood movie sees Clint play a bad ass but sort of out of it newspaper reporter looking to get a wrongfully convicted man off death row. It's the kind of role I thought I'd never see him play. Clint as a newspaper reporter? Does he carry a gun and beat the crap out of people? No, no he doesn't do any of that stuff. Clint runs down leads, looks for the truth, and, when he isn't jawing with Jimmy Woods (best scenes in the movie hands down. Watch Woods eat that candy bar) he's having an affair (Clint likes to bite asses). And then there's the scene where he pushes his kid on the bike. I never thought I'd ever see Clint Eastwood do that in a movie. This movie didn't make much money at the box office when it came out, and it's generally considered an Eastwood miss. I think the movie needs a reexamination. It's way better than its reputation.
4. Letters from Iwo Jima (2006)
Not only Letters from Iwo Jima one of the best World War II movies ever made, it's also one of the best war movies ever made period. Instead of doing yet another movie about the American war experience, Eastwood looks at the war from the perspective of the Japanese. We see them fight for their country, for their honor. They aren't portrayed as sadistic psychos. They're just people fighting for a cause. Great, thoughtful stuff. I am kind of surprised, though, that when people discuss this movie they don't mention the scene where the Japanese soldiers blow themselves up with their own grenades. It's one of the most disturbing scenes in war movie history. And who can forget that flashback scene where Ken Watanabe's character has to assure a room full of American military officials that Imperial Japan has no interest in attacking America. That was brutal, too.
3. Any Which Way You Can (1980)
The second and final Philo Beddoe movie has Philo, along with Lynn (Sandra Locke), Orville (the great Geoffrey Lewis), and Clyde the orangutan, looking to score big after fighting William Smith's uber bad-ass Jack Wilson. The build up to the big fight is great stuff, as we see various people "in the know" setting up their bets and looking to see the big fight. And there's the Black Widows motorcycle gang led by big, fat Elmo. Remember the scene where they're all pulled over by the cops and the cops laugh at them because they're all wearing bad wigs? Awesome stuff. And there's the friendship that Beddoe develops with Wilson. Why are they jogging together? Why aren't they constantly at one another? You don't do that in their business, I guess. It's too bad that Clint and company didn't make a third one. I bet it would have been a blast.
2. Magnum Force (1973)
Magnum Force, the second Dirty Harry movie, is chock full of great stuff. There's Eastwood as Inspector Harry Callahan, of course, kicking ass and taking names like only he can. There's the Magnum Force, the vigilante motorcycle cops taking out various bad guys (and other people) across the city under the leadership of Hal Holbrook's Lt. Briggs. You've got Hutch (David Soul), Otter (Tim Matheson), Dan Tanna (Robert fucking Eurich), and the Kip Neven as those vigilantes, blowing people away with their silenced .357 magnums and, on occasion, sub machine guns. And there's the big reveal on the Dirty Harry character towards the end, when we find out that Dirty Harry isn't the cold hearted fascist that "we all assumed" he was after the first movie. He tells Briggs that while he hates the law because of its loopholes, he's going to keep following it until someone comes up with something better. He doesn't really believe that anyone is or should be above the law. "A man's got to know his limitations." Easily the most important "Dirty Harry" movie of the five made (you shouldn't watch Dirty Harry without also watching this so you can get the full Dirty Harry experience).
1. Heartbreak Ridge (1986)
When most people think of Clint Eastwood they either think of the "Man with No Name" character from Sergio Leone's westerns or Inspector Harry Callahan from the Dirty Harry movies. When I think of Clint, I always first think of Heartbreak Ridge and Gunnery Sgt. Tom Highway. He's a bad ass war hero with a serious drinking problem, a generally poor attitude, and endless self-inflicted female problems. He's seen it all, done it all, and he takes absolutely no shit. But he's also interested in what you could call self-improvement. He reads women's magazines to find out what went wrong with his marriage (he doesn't want anyone seeing him do it, though. When someone asks him about the magazines Highway always says that they belong to someone else). He also shows sympathy for a Marine with money issues (he doesn't get him thrown out. He finds a way to keep him around. Highway isn't much of a kid guy, though). It's Eastwood's greatest role.
The movie is also chock full of great lines. "Shut your face, hippie." "I said don't give the prick the satisfaction, sir." "How about I just bend you over the table and nail you in the keister? That's your persuasion, you just said so. I'll send you home with a 'Just pumped the neighbor's cat' look on your face." "His mama know he's playing Marine?" "What's your assessment of this exercise? Clusterfuck." "Webster, the only thing you could build is a good case of hemorrhoids." "You're dead marine, you just got your legs blown off and we'll have to send out a search party for your testicles. Now, where's your backup?" "This is the AK-47 assault rifle, the preferred weapon of your enemy; and it makes a distinctive sound when fired at you, so remember it." And, of course, "It means be advised, that I'm mean, nasty, and tired. I eat concertina wire and piss napalm. And I can put a round through a flea's ass at two hundred meters. Now why don't you go hump some other leg mutt face before I push yours in."
Great stuff. How are those lines not on a line of T-shirts?
"Improvise! Adapt! Overcome!"
5. In the Line of Fire
This 1993 thriller had Eastwood embracing his age as an elderly Secret Service agent who finds himself in a cat-and-mouse game against John Malkovich's twisted killer out to shoot the President. Eastwood uses his drive with wry humor and a good chemistry with Rene Russo but the scenes where he and Malkovich talk on the phone are more thrilling than any action bits. The final showdown is great but it's the build that makes this stand out as one of the best thrillers around and helped invigorate Eastwood as a box office star once more.
4. Letters From Iwo Jima
It remains a great irony that in 2006, much hype was made over Flags of Our Fathers, a tale of the U.S. forces who raised the flag on Iwo Jima. But it was the other film that ended up being a Best Picture contender, which makes sense as it is the better of the two. Telling of the attack from the Japanese perspective, Eastwood humanizes the "enemy," letting us see how these men were fighting for their own countries and the traditions of their people. Ken Wanatabe is great as the commander who knows he's doomed but determined to fight to the end and the battle scenes show the brutality of war and how these conflict was nowhere as clear-cut as historians say.
3. The Good, the Bad and the Ugly
The movies that made Eastwood a star, the last of the "Man With No Name" trilogy still stands as a fantastic and gripping tale with Eastwood's character getting involved in the search for treasure with two unlikely "partners" who'd as soon kill him as help him. From Civil War battlefields to wide open ranges, all set to that classic musical score, it's a stunning film that pushes the Western to new heights. This is the Eastwood we know, the gritty drive, the sneer, the cool attitude, blowing away guys without batting an eye, a fantastic final duel, this is a movie that still stands as Eastwood unleashed and continues to enthrall every time you watch.
2. Million Dollar Baby
Released to almost no advance hype in 2004, Eastwood's boxing drama soon became the most acclaimed movie of that year. At first, it seems a take on Rocky with Eastwood the veteran trainer helping Hillary Swank's feisty young lady become a champion. But with a sudden and horrifying twist, the final half hour is a gripping tale of the human spirit and the question of life. Swank and Morgan Freeman won Oscars for their roles and Eastwood earned a second Director and Picture combo for a film where he also turned in a fine performance as a man opening his heart only to see it break much like the audience watching this amazing work.
In 1992, most critics were declaring the western dead. Then Eastwood came along and elevated it to a new work of art. The story of a former gunman coming out of retirement to accept a bounty on the men who cut up a prostitute is brutal and bloody yet with surprising heart. Eastwood himself is fantastic in the lead and backed by a first-rate cast with Morgan Freeman as his friend and Gene Hackman in his Oscar-winning performance as a brutal local sheriff. It brings up the old line of how "when legend becomes fact, print the legend" and it deserved its Oscars for Best Picture and Director as Eastwood lets the west come alive in its brutal glory.