I also highly recommend "I Never Sang For My Father", if you can find it.
I think "Another Woman" is vastly underrated, and one of Woody's best, just behind "Manhattan", "Interiors", "Hannah...", "Crimes &...".
I loved "An Unmarried Woman" by Paul Mazursky as well. His "Alex In Wonderland" is a terrific one as well, from the male point of view about a filmmaker.
More recently, I loved "the Visitor", with a quiet but terrific perf by Richard Jenkins as a middle-aged widower.
Paul Newman was just mentioned above, and one of my faves is "Mr. & Mrs. Bridge" from the Ivory-Merchant team, about a couple that starts out at about middle-age and works up about 20 years. I think that's a fascinating movie.
I don't think "middle age" is the big theme so much as it is about how "coming-of-age" is something that can happen to us several times through life and not just when we move from tweendom to teenager land.
Oh yes, and "Sunday Bloody Sunday" from John Schlesinger about a love triangle with two middle-aged types competing for a grad student type. That's another great character study.
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