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Originally Posted by Stealhead
I really like Gran Torino
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My personal favorite would be
The Outlaw Josie Wales. That said, have you ever seen
The Beguiled? Not his best film by a long shot, but the only one I know of in which he is actually the bad guy. If you haven't seen it, give it a shot.
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True Eastwood is a fairly good director as well.
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I would say that
Letters From Iwo Jima puts him in the ranks of the truly great directors.