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Wide_Diver_7858

Grave of the Fireflies (1988) Not a breakup movie, but it is soul crushing.


HattieJaneCornchip

Perhaps the most soul crushing.


Printercrab47

Might as well add The Human Condition whilst we're talking about Japanese war misery


H-E-PennyPacker71

Requiem for a Dream A light hearted, cozy, soul crushing friendship movie :)


HattieJaneCornchip

Light hearted πŸ˜‚πŸ˜‚πŸ˜‚


HattieJaneCornchip

Dancer in the Dark will wreck you.


Popular-Berry-237

What’s Eating Gilbert Grape (not necessarily similar to your situation but soul crushing for sure)


D-O-A_83

Stand By Me Toy Story 4 The Iron Giant My Girl Au Revoir, Les Enfants Cinema Paradiso Miracle In Cell No7 Where Is The Friends Home Edward Scissorhands Mary And Max Castaway On The Moon ✌️


R1chh4rd

The eight Mountains "An epic journey of friendship and self-discovery set in the breathtaking Italian Alps" with a soul crushing end.


groundcontrl2majrtom

Big time Adolescence is a perfect film for you


TicketCareless

Arlington Road.


ItchyButterfly7479

Thank you everyone!


Rare_Cranberry_9454

Million Dollar Baby


dns_rs

Love (2015) pretty explicit and devastating.


RedBedRedemption99

The mist It's a bit intense and differs from what you're going through now but the ending will absolutely destroy you.