Fanny and Alexander, 5-hour version.
This.
Great flick.
I’ll never watch it again.
For some reason, Lynch’s films aren’t Bleak to me. Dark, but not bleak. Von Trier on the other hand… Anyone watch Antichrist? Yeesh.
Eden Lake. We watched it because it had gotten good reviews and we were in the mood for a horror movie, but the end was horrible. It’s the kind of ending that lingers in your head and makes you want to take out your brain and scrub it.
Anyone for Antichrist?
Want to test & see if somebody is a sociopath?
Show them Grave Of The Fireflies.
If they don’t break down weeping during that film, they should be in a straightjacket.
Treeless Mountain is a movie that’s bleak without being disturbing or violent. Just a hopeless situation for two little girls. I think it’s all the more depressing because it doesn’t feel all that extraordinary.
Happiness, but in a good way. And Fantastic Planet, in a bad way. I don’t know if it’s bleak as such, but it did leave me unsettled and miserable as per spec.
I haven’t seen most of the other films mentioned in the thread.
For me, it was Beyond the Mat, the wrestling documentary.
First time I saw it I broke down in the first two minutes.
You can also make someone think you’re heartless when you point out that Seita largely brought it on himself. The director is in agreement with this viewpoint, however. That’s something that’s more easily caught on a second viewing.
I caught that, too…
And I force my mind to see it as a metaphor for Japan at the end of WWII. Give it up and go to the bank (surrender to the US), rather than stubbornly hang on and be devastated. If I take it literally, it makes me more upset.
“Grapes of Wrath”. In spades.
Man on Fire with Denzel Washington. I couldn’t finish watching it and got a friend to tell me how it ended.
“El Norte” (old) It’s like “A Better Life” without a good ending.
“The Good Life” with Mark Webber and Zooey Deschanel. What he does while waiting for his life to begin—he discounts the good compared to his bad past—and what he does with the ______ bequeathed to him by his father—it’s bleak until the last minute when it made me fist pump. Kind of a “One Flew Over the Cuckcoo’s Nest” moment.
+1 for All Quiet on the Western Front. I watched it once, and cried so much that I gave myself a splitting headache. Kept the VHS tape for many years, but never once felt the urge to put it in again.
When the wind blows, absolutely heartbreaking and gut wrenching watching this lovable elderly British couple endure the effects of radiation sickness from a nuke strike…
<weak anld halting> “Maybe we should get into…the…paper…bags…again…”
Se7en deserves a mention.
But Breaking the Waves gets my vote. Followed by Dancer in the Dark. Lars Von Trier is an ass. Why does he think viewers want to wallow in misery?
Gotta be Alexandro Jodorowski’s El Topo (not to be confused with the rather non-bleak Topo Gigio material).
This film would be terminally, massively bleak if it weren’t so damn crazy, and full of itself. The Russian roulette scene in church is downright funny, at least if you’ve been watching El Topo for an hour or so already and you’re still there 
I came here to nominate Breaking the Waves, Lars Von Trier is indeed an ass. Will watch no other film by him. Like a lot of European filmmakers, he seems to want to hurt the audience. Not worthy of anyone’s time or attention.
I’ll nominate one that I have not yet seen mentioned in this thread, They Shoot Horses Don’t They?
Seventh Seal in my opinion or Dr. Strangelove