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10. Mystic River (2003)
With Clint Eastwood behind the camera and Sean Penn, Tim Robbins, Kevin Bacon, and Marcia Gay Harden in front of it, the film adaptation of Dennis Lehane's Mystic River was pretty much a gimme for one of the highest-profile releases of 2003, and it didn't disappoint, netting four Oscar noms (and two wins), almost $100 million in domestic gross, and enough positive reviews to earn an 87 percent Tomatometer. Although critics were quick to point out that Mystic River doesn't equal or surpass Eastwood's finest work, his trademark no-frills approach made a good fit for the source material, and the performances from the stellar cast were as strong as you'd expect. Empire Magazine's Alan Morrison reflected the sentiments of many of his peers when he wrote, "While not quite the equal of the novel, it's more complex, emotionally-charged and better acted than the average Hollywood thriller."
9. White Hunter, Black Heart (1990)
8. The Bridges of Madison County (1995)
7. Million Dollar Baby (2004)
6. Honkytonk Man (1982)
5. Pale Rider (1985)
4. Letters From Iwo Jima (2006)
In 2006, Eastwood had World War II on the brain - specifically the Battle of Iwo Jima, which he memorialized with a pair of movies, Flags of Our Fathers and Letters From Iwo Jima. Where Flags presented the battle in a series of flashbacks, Letters put viewers right in the thick of the war - and did it from the Japanese side of the line. It was a risky choice, both commercially and in the context of the political tenor of the times, but for Eastwood, it made nothing but sense: Having long examined the grim and terrible realities of violence in his films, here he siezed the opportunity to present the savage costs of war for soldiers on both sides. The approach fit neatly into Eastwood's moral relativism, reinforcing his long argument that no matter how noble your reasons for unleashing it, violence takes an unavoidable toll. Letters, like Flags, wasn't a huge box office draw, but critics responded positively - as Paul Byrnes of the Sydney Morning Herald noted, even alongside Eastwood's previous triumphs, "Letters is an extraordinary achievement" - and it earned four Academy Award nominations.
3. High Plains Drifter (1973)
2. Unforgiven (1992)
Seven years after revisiting the Western with Pale Rider, Eastwood made one final return to the genre - and what a return it was. Even by its director and star's inflated career standards, Unforgiven was a smashing success, going on to win Academy Awards for Best Picture, Best Director, Best Editing, and Best Supporting Actor - and, ultimately, to enshrinement in the United States National Film Registry. Viewed in the context of Eastwood's unsentimental Westerns, Unforgiven represents the ultimate deconstruction of the genre's myths, presenting Eastwood as an aging gunslinger whose soul has been irrevocably stained by the violence of his past. It contains some of his best work as both a director and an actor, and is, in the words of Time Magazine's Richard Corliss, "Eastwood's meditation on age, repute, courage, heroism -- on all those burdens he has been carrying with such good grace for decades."
1. The Outlaw Josey Wales (1976)
10. Mystic River (2003)
With Clint Eastwood behind the camera and Sean Penn, Tim Robbins, Kevin Bacon, and Marcia Gay Harden in front of it, the film adaptation of Dennis Lehane's Mystic River was pretty much a gimme for one of the highest-profile releases of 2003, and it didn't disappoint, netting four Oscar noms (and two wins), almost $100 million in domestic gross, and enough positive reviews to earn an 87 percent Tomatometer. Although critics were quick to point out that Mystic River doesn't equal or surpass Eastwood's finest work, his trademark no-frills approach made a good fit for the source material, and the performances from the stellar cast were as strong as you'd expect. Empire Magazine's Alan Morrison reflected the sentiments of many of his peers when he wrote, "While not quite the equal of the novel, it's more complex, emotionally-charged and better acted than the average Hollywood thriller."
9. White Hunter, Black Heart (1990)
8. The Bridges of Madison County (1995)
7. Million Dollar Baby (2004)
6. Honkytonk Man (1982)
5. Pale Rider (1985)
4. Letters From Iwo Jima (2006)
In 2006, Eastwood had World War II on the brain - specifically the Battle of Iwo Jima, which he memorialized with a pair of movies, Flags of Our Fathers and Letters From Iwo Jima. Where Flags presented the battle in a series of flashbacks, Letters put viewers right in the thick of the war - and did it from the Japanese side of the line. It was a risky choice, both commercially and in the context of the political tenor of the times, but for Eastwood, it made nothing but sense: Having long examined the grim and terrible realities of violence in his films, here he siezed the opportunity to present the savage costs of war for soldiers on both sides. The approach fit neatly into Eastwood's moral relativism, reinforcing his long argument that no matter how noble your reasons for unleashing it, violence takes an unavoidable toll. Letters, like Flags, wasn't a huge box office draw, but critics responded positively - as Paul Byrnes of the Sydney Morning Herald noted, even alongside Eastwood's previous triumphs, "Letters is an extraordinary achievement" - and it earned four Academy Award nominations.
3. High Plains Drifter (1973)
2. Unforgiven (1992)
Seven years after revisiting the Western with Pale Rider, Eastwood made one final return to the genre - and what a return it was. Even by its director and star's inflated career standards, Unforgiven was a smashing success, going on to win Academy Awards for Best Picture, Best Director, Best Editing, and Best Supporting Actor - and, ultimately, to enshrinement in the United States National Film Registry. Viewed in the context of Eastwood's unsentimental Westerns, Unforgiven represents the ultimate deconstruction of the genre's myths, presenting Eastwood as an aging gunslinger whose soul has been irrevocably stained by the violence of his past. It contains some of his best work as both a director and an actor, and is, in the words of Time Magazine's Richard Corliss, "Eastwood's meditation on age, repute, courage, heroism -- on all those burdens he has been carrying with such good grace for decades."
1. The Outlaw Josey Wales (1976)
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