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Well that's pretty tough, I was raised on Eastwood and I can't tell..
The Good The Bad and the ugly would be my favourite western, but then again WHO is bigger in the western genre after the John Wayne era than Clint? Unforgiven would be one great anti hero western in my book too..
Dirty Harry - can't get wrong with that one, I guess i have seen all the Dirty Harry movies and I suspect myself from seeing them even more than once.
From his latest work - Million Dollar Baby was kind of touching, I wouldn't expect such a theme to have such depth, just brilliantly made movie.
As the least typical movie he ever made as a director - that would have to be his flick about Charlie Parker with Forrest Whitaker, I guess it was called "The Bird" and it was a great movie for those who know a bit about the bird.
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