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I'm not sure if it's been mentioned but Requiem for a Dream is pretty depressing all around.
The ending of the most recent Star Wars Rogue One is pretty depressing, too, (pretty much the last 5-10 minutes) even if at the very end there is the glimmer of hope as we all know what ultimately happens.
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The ending of the original "Oldboy" shattered me. One of the most difficult scenes to a film I've ever watched.
"Requiem For A Dream" ending was BRUTAL.
Mulholland Drive was trippy as hell, I was more blown away than crushed. But I couldn't believe what I had just experienced. David Lynch is a god damn genius.
Relatively obscure movie despite the fact it had Kevin Costner and Clint Eastwood in it, A Perfect World. Loved the movie, but damn was it sad at the end.
" Christmas in August". A little know Korean film made in 1998. A thirty something man who ekes out a modest living as a portrait photographer makes a connection with a young parking police offer. Unfortunately the man is suffering from a slowly progressing fatal disease. Both parties begin to fall in love but the man abruptly ends the relationship because he has no future. He does not tell the young women why he ended the relationship. He dies and life goes on.
Charly (1968) with Cliff Robertson, wherein a man with an IQ of 69 undergoes an experimental surgery that results in a rapid IQ increase to genius level. His teacher (Claire Bloom) falls in love with him on a peer level, they have a great future, but then he starts to lose intelligence--and he understands the full implication of this---and ends up back to baseline, and basically forgets who he was when he was brilliant.
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