1. Unforgiven (1992, Clint Eastwood)
I balk at selecting this for #1. No critic wants to be so obvious, but the fact is that this movie redefined Westerns, and redefined Clint Eastwood. It's a milestone both in his career, and in movie history.
2. The Bridges of Madison County (1995, Clint Eastwood)
OK. Now I get to be not so obvious. This should have been a dud, and it would have been, if one of its original directors (Steven Spielberg, Bruce Beresford, etc.) had finished it. But Eastwood gave it a sense of earthiness, and gave Meryl Streep arguably her best role, ever. At its core, it's a goopy romance, but it stings, and bleeds, and it feels honest.
3. Million Dollar Baby (2004, Clint Eastwood)
This one is pretty well loved, but some love it -- and its detractors hate it -- for the wrong reasons. It has come to be seen as a message movie about the right to die, and certainly the final stretch of this movie contains some powerful stuff. But the real reason it's great is because it's one of the great low-rent boxing movies.
4. The Dollars Trilogy (1964-66, Sergio Leone)
Why quibble over which of these so-called spaghetti Westerns is the best? The truth is that I'm often in the mood for one or the other of the three, and all of them contain moments of greatness. How could I choose the epic masterpiece The Good, the Bad & the Ugly and never again see the "you better get three coffins ready" scene in A Fistful of Dollars?
5. The Beguiled (1971, Don Siegel)
Eastwood made five movies with Don Siegel, and they're all great; Eastwood seemed to bring out the best in Siegel, and vice-versa. I'm winging it and picking this one as the best merely because it's so atypical, focusing more on Eastwood's psychological/sexual side. It's also their most harrowing film.
6. A Perfect World (1993, Clint Eastwood)
Coming just months after two big hits and two Oscars, this movie was somehow mostly ignored. It's a kidnapping movie, with Eastwood playing a cop, but it's somehow expanded, and turned on its side. It's more of a moody epic, and a deconstruction at the same time. Perhaps it was just too difficult to define, but it's a masterwork nonetheless. (And it contains Kevin Costner's finest performance.)
7. White Hunter, Black Heart (1990, Clint Eastwood)
One of Eastwood's biggest flops, this deconstruction of filmmaking and manliness contains arguably his first great performance, doing a kind of quasi-combination of himself and John Huston. It shows the regular indulgence of a successful moviemaker's whims, but this time with a heavy price.
8. Dirty Harry (1971, Don Siegel)
It's hard to ignore the impact of this great cop movie, which some critics labeled as "fascist." I believe it's more Libertarian in its attitude. Either way, it clicked with audiences, and still does. It spawned four sequels and at least two catchphrases.
9. Hereafter (2010, Clint Eastwood)
A controversial choice, which I selected as the best movie of 2010. I believe that with better marketing and timing, others would have joined me. I love the gentle, spiritual aspect of this movie, and that the characters all seem to have inner lives; they exist on a slightly slower plane than the rest of us. They have time to think and feel.
10. Gran Torino (2008, Clint Eastwood)
Oddly, Eastwood's last acting role (to date) was also his highest grossing movie. But despite its success, it was still misunderstood, disregarded as just another action movie. But in its way, it was as canny a deconstruction of myth as Unforgiven.
That leaves me with 10 more great movies, in alphabetical order: Bird (1988, Clint Eastwood), Coogan's Bluff (1968, Don Siegel), Escape from Alcatraz (1979, Don Siegel), In the Line of Fire (1993, Wolfgang Petersen), Letters from Iwo Jima (2006, Clint Eastwood), Midnight in the Garden of Good and Evil (1997, Clint Eastwood), The Outlaw Josey Wales (1976, Clint Eastwood), Play Misty for Me (1971, Clint Eastwood), Thunderbolt and Lightfoot (1974, Michael Cimino), Two Mules for Sister Sara (1970, Don Siegel). And there are yet more...
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