I don't usually get emotional at movies but Cinema Paradiso (specifically the 2h53 Director's Cut version, which is extra sad) got me like
Threads (1984) - about living through nuclear fallout
Requiem for a Dream (2000) - about desperation, loneliness and addiction
The Wolf House (2020) - about Colonia Dignidad
Skinamarink (2023) - about children who wake up in their family home and their parents have disappeared, as have all the windows and exterior doors
Woah, thanks for the lead on Skinamarink. Looks extremely cursed.
It's fucked, but I will warn you it's about as hated as it is loved. If you want to watch it and you don't have the option for a theatre I highly recommend keeping your phone in the other room and closing all your tabs - it kind of demands you give it your full attention to allow it to sink into your psyche.
My idea of "sad" is probably a bit abstract, but here are a few off the top of my head:
- The Fountain
- Vanilla Sky
- House of Flying Daggers
- Gattaca
- Hero
- Eye of the Beholder
Grave of the Fireflies. Haven't watched it, but heard a lot of things.
- Manchester By The Sea
- Irreversible
- Gone Baby Gone
- Instructions Not Included
Ghost World and it's spiritual successor The Last Black Man in San Fransisco. They're not portraits of despair, but they have an underlying melancholy and poignancy that affected and stuck with me me more than most tragedies I've watched.
Definitely will check out that spiritual sequel. I mever heard of it.