Films with MASSIVE downer endings.

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No one does the massive downer ending like CLAMP, imo.

Fat Girl
No surprise there, since almost the entire film is a massive, icky downer. I'm still glad Catherine Breillat exists to explore those feelings, though.

Sonatine
This one has plenty of happy moments and excitement, but the more I think about it, there was no other possible ending.

Inland Empire
I'm like, really? I watched all that for this? It was a downer for me because I consider it an emotionally immature pile of self-indulgent nonsense. It had some great imagery, but once I perceived how simple the story really was I felt let down.

No Country For Old Men.

The protagonist not only doesn't get away with the money, but gets killed, and his wife very probably gets killed, too. The antagonist hitman only gets a compound fracture of the arm, but otherwise escapes unpunished with the money. And the sheriff investigating the whole mess never comes close to solving the multiple homicides, let alone understands why it all happened.

Watching the second time, I noticed Chigurh wipes his boots off when he leaves the house at the end.

The Homesman

The Grey

The endings of these two were massive letdowns. Not just because of stuff that would be considered plot spoilers, but because the ending plots were convoluted and too open to interpretation.

Bone Tomahawk, I don't know if I would call it a major letdown but it just kinda happened lol. Would've been nice to see their lives afterwards, for at least 5 minutes or so. There may be a sequel in the works. That's the only explanation I can think of.

Not a film, but an anime

Ga Rei Zero

The first two episodes tell the end of the story, so you get all that right up front. If you can survive those two, then things settle down for a while. I haven't actually made it through the series twice, yet. It's sort of a terrible feeling, watching the story develop, knowing that you've already seen the end, and it isn't nice.

Old Yeller

Million Dollar Baby

Clannad [the movie]; though I like the anime better
Grave of the Fireflies
5 Centimeters Per Second

Most of the movies I watch have bittersweet endings instead of downer endings.

Greg Araki's Doom Generation

Marley and Me

End of Evangelion.

The Wrestler

Fail Safe
The Day After
Threads
On The Beach
Love Story

Old Yeller
Marley and me
My Dog Skip
Hachiko
Turner & Hooch

When the wind blows
Pokemon Heroes
Lucario and the mystery of Mew

The odd life of Timothy Green

1984
On the Beach
Threads

I don't think I've seen any of these films/shows, not even the family-friendly ones. All I can think of is literally any TV show that gets cancelled by its network before it really ends.

I just watched a movie called Bad Match on netflix and I would say it had a pretty big downer ending...but I don't really want to spoil it for people who haven't seen it. I mean it really kind of defeats the purpose of a psychological thriller if someone gives away the ending but it was brutal.