Maybe not as bleak as some of the others mentioned here, but worth a nod, is the brilliant Coen brothers movie A Serious Man. A great dark comedy. And just when you start to think things will come out OK for the main character, uh, well, they don’t.
Worse than Samaria, is The Isle, by the same director.
But neither compares to the vileness that is Bad Guy. Virginal college student is kidnapped, raped, and forced into prostitution. The fellow is a vile, sick excuse of a human being. You just feel so bad for her. But then she (I guess) falls in love with him or something. In any event, she, on her own volition, follows to be with him. Sick movie with a sick message. I wanted to curl up in the shower for a week after watching that.
I was completely unaffected by the film except for the very last shot of the female lead cuddling with a bag of drugs (coke? can’t recall). Everything else I was like “well, that kinda sucks”, but that single shot hit me hard for some reason.
ETA: Due to this thread, I watched Grave of the Fireflies last night. Let’s just say that I (re)watched Les Mis with my mom today and thought “huh, this is a rather uplifting movie.” (Not that Les Mis was ever on anyone’s “bleakest production ever” list, but still, I wouldn’t normally consider it a happy go lucky movie)
I’m normally pretty sensitive when I watch films, but I disliked every character in Requiem for A Dream, except the Mother, so much, that while I certainly found it a sad story to witness, I wasn’t all that affected by any scenes except those involving her. The rest of the addicts were just such selfish jerks.
Bad Timing, by Nicolas Roeg… hit me pretty hard. I hung in until one of the last scenes, then ran out of the room almost in tears.
I felt the same way, generally. I think part of it was I watched it with my girlfriend and we were still in the honeymoon phase of our relationship, and the notion that she abandoned her boyfriend and replaced him with drugs (that she loved so much she cuddled with) hit me really hard. It probably wouldn’t faze me nearly as much anymore.
This^ plus, I found it way too anvilicious to take seriously. Seen more subtlety in D.A.R.E. presentations. Loved the soundtrack, though.
The Deer Hunter hasn’t been mentioned. I saw it once, and I am glad I saw it, but it left me depressed for approximately six weeks following. I’ve never watched it again.
Yep. I found it too utterly cartoonish to be bleak. It was basically an after-school special with nudity.
Wages of Fear was pretty bleak.
Yeah, but…I’m kidding but you’re not wrong that it is a very somber movie. I watch it about once a year, though, and find some joy in it. Kind of like The Last Waltz – you know what’s going to happen, but there are enough fun parts that keep you watching.
You want bleak? Try The King of Comedy. I’ve been watching it since I was a kid but at one point in my 30s I realized it is a movie about the terrible things that happen to those people you kind of walk by on the street and ignore.
Requiem? No joke, but I saw it when I was blasted on liquor or weed and the fantastic elements on retrospect seemed to set the movie on its right end for me. I still can’t get through Pi though, by the same director. That one is too bleak.
Agreed. Also those people have never heard of Theseus.
A second vote for The Grey Zone. A good film, but I don’t want to see it again. There are some truly horrific scenes in that movie, along with a downright depressing ending. 
I really shouldn’t be using this thread for film recommendations, but I can’t resist. However, when I looked up “The Grey Zone” I saw David Arquette was the first billed. Is he the main character? Because I don’t think I can take it seriously if he’s the main character.
I have also added “Grave of the Fireflies” to my reading queue.
People who have Grave of the Fireflies on their ‘to watch list’. Good god, don’t watch it. If you own it, sell it. I don’t care that it’s a ‘good’ movie, or that it was so well done. It’s depressing as hell. It makes you just want to curl up and try to mentally erase the entire movie from memory. I watched it once and never ever again. Especially now that I have a kid, there’s no way in hell I could stand watching it.
No mention of “a serbian film”? I can still destroy a couple of my friends moods with a simple utterance of the phrase “start with the little one”. That is probably the only film i took the trouble to seek out that i completely regret.
It looks like Leaving Las Vegas is winning the bleakest movie vote so far. I"ll give it another one.
Goddamn I have never felt more crappy after seeing a movie.
Irreversible and Funny Games 2007 version are a close second and third. Although Naomi Watts running around in her underwear for half the movie wasn’t all bad. 
Eh, I know I’m going to see like a callous sociopathic bastard with no soul, but I really think it’s that good. It’s really a subtle, intricate, layered movie. Don’t get me wrong, it was really depressing and horrifying, but there’s just so many little things, and I picked a lot of them up the first time around. I think I’d catch more on another watch.
It’s probably different if you have kids, definitely, but I think it’s a masterpiece and someday I might watch it again just so I can analyze the hell out of it. I think I may have been somewhat tempered by the hype it gets (“the best movie I never want to see again” and all that).
It’s somewhat more horrifying when you realize it’s semi-autobiographical, and ultimately is about a guy suicide-by-fiction because of his demons, but there’s just so much depth to it that it’s amazing.
ETA: Though I fully admit that I had trouble sleeping the night after I watched it. I wouldn’t say I had nightmares, but it definitely made me toss and wake up a lot because of how disquieting it was.
In another thread, I mentioned a 1966 treatment of “Alice in Wonderland.” (Hell, just look at the sad expression on the actress’ face in the picture!)
Basically, the acting is wooden, flat, unemotional, and dreary. Since the cast includes a number of VERY good actors, the blame must go to the director. He must have told the actors not to show any emotion!
The actors also spend a lot of time looking past each other. They don’t make eye contact!
This “dead serious” style takes away any of the fun of the original stories. The “caucus race” scene looks more like a visit to a real madhouse of the Victorian era: not fun at all!
The only shining bit in the entire film is Leo McKern as the Duchess (!) He simply ignores the director, and allows himself to act, doggonit!
Otherwise, this is one goddamn bleak stinkin’ movie.
Kadosh. Incredibly depressing Israeli film about two ultra-Orthodox sisters from Mea Shearim.
I also have to put in a third voice of support for The Grey Zone. I know this thread doesn’t include Holocaust movies, but wow. That movie made Schindler’s List look uplifting and inspirational. We watched it for a seminar in college and I had to wander around campus aimlessly for an hour afterward to calm down.
Based on the comments so far, is anyone else actually wanting to see some of these movies now?
I’ll add another : “Jacobs Ladder”
You mean, what fictional, fantasy wolves with behavior that does not resemble actual wolves do very well in a nightmare that has nothing to do with reality.