I have to go with “The Story of Us” Bruce Willis and Michelle Pfeifer.
Unfortunately, I cried my eyes out during this one, because it reminded me way too much of my parents while I was growing up. I think it was healthy though.
Also in the category of “losing all humanity”, the somewhat overlooked Miracle Mile, with Anthony Edwards.
Just happened to see Casino again last night and found myself thoroughly depressed by the end, although it is unclear whether this was because of the complete unlikability of the characters or simply its interminable length. What a catalogue of self-inflicted misery, though.
“Breaking The Waves” in which Emily Watson suffers horribly at the hands of a cruel religious community, has to be one of the most moving films ever (despite director Lars Von Trier’s constant ironic devices). Von Trier’s “Dancer in the Dark” is also quite moving, but a bit more contrived.
“Sling Blade” (in which Billy Bob Thornton is a simple-minded murderer) also had me crying loads. As did “The Royal Tenenbaums”, though neither are primarily tearjerkers.
(On the other hand, “Terms of Endearment” has to be the least tragic intended-weepie ever.)
“Artificial Intelligence” - for two reasons. Neither is enough to nominate it by itself, but both together is depressing:
David spends all of eternity praying to the blue fairy in vain. That is the end of the movie. Ignore the spielburg-esque alien scene. That’s just a mass hallucination.
The second reason is because of spielburg’s desecration of what would otherwise have been a half-decent movie. Everytime I think of it I get depressed.
“Butcher Boy,” directed by Neil Jordan, based on the novel by Patrick McCabe. The film, by the way, is a regular light-hearted comedy compared to the book (or any of McCabe’s other books).