Before 1970: Lonely are the Brave (1962). Gah! I love love love this movie -- until the last five minutes. Then I hate it, because my heart aches and breaks, and I'm sad for days afterwards. But Kirk Douglas, that absolutely gorgeous horse, Whiskey, and one of my all-time favorite Jerry Goldsmith scores make this movie awesome despite the fact that the ending kills me even when I know it's coming.
Post 1970: Er... I can't seem to think of one. I can think of plenty of movies with sad moments, but none of them leave me feeling sad afterwards. They ultimately end happy. I can think of several downright depressing movies, but that's not the same as sad. I'm sure I'm overlooking one, but after thinking on this for a few days, I still can't come up with one. Hm.
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How about Michael Keaton in, The Merry Gentleman (2009)? Or, Bud Cort in Robert Altman's, Brewster McCloud (1970)? And here are a few more to ponder:
Love Story (1970)
Birdy (1984)
Jacob's Ladder (1990)
JFK (1991)
The Bridges of Madison County (1995)
The Reader (2008)
And who can forget the sadness of losing the president that we never had in Emilio Estevez's, Bobby (2006), about the last day of RFK: "Some people see things as they are and ask 'Why?'. I dream of things that never were, and ask 'Why Not?'"
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