Nothing eases a head cold like a good cry and with three days of Air Quality Red Alerts here in central North Carolina, I thought I better get your suggestions now... My pick, hands down, is the documentary Dear Zachary: A Letter to a Son About His Father. I'm not even going to begin to describe it because I will start crying, it's that moving... angering... just sad. You see the best and absolute worst of people all in one sitting.
Most depressing and heavy movie I've ever seen. I couldn't even get all the way through it. It's good, but it is so heartbreaking from start to finish.
LOVE Diving Bell!! Also really enjoyed both 21 Grams & Babel... had no idea they shared a director! As haunting as those two are, I think Biutiful trumps them. Completely believe that about Bardem's performance, he was beyond heart-wrenching, a genius. I will definitely find Amores.
Wit is another good film about death, completely different approach though...
Do see Dear Zachary! But only if your up for a good depression and if you want the full impact of misery, try not to learn anything about it before you see it... my boyfriend was familiar with the case so was spared a bit.
I try to stay away from sad movies now, and can't remember a lot from my younger days, but I do remember watching a couple of versions of the movie "Of Mice and Men". They were sad.
I'd tie between Aftershock and Bent.
Aftershock is a Chinese Sophie's Choice, except that the child she chooses to die miraculously lives, unbeknownst to the mother and surviving sibling.
Bent is about a gay concentration camp inmate. Super spoilers ahead: While attempting to cross the border with his boyfriend, Max and he are caught and put on a train, presumably to Dachau. Another man on the train tells Max that if he can survive the trains, then he has a chance of surviving the entire thing. Knowing that Rudy was Max's boyfriend, the German guards start to beat him up, and give Max a club, ordering him to beat his boyfriend. After a few hits, Max bludgeons his boyfriend to death quickly. The guards take Max into the back, and tell him that since he is gay AND a Jew, they will give him a yellow star rather than a pink triangle (since "they're the lowest in the camps"), IF he proves that he is straight. They took one of the female corpses off the train, and they have him have sex with it, laughing at him all the way. When he gets to the camp, they place him in a work position meant to drive him mad. Two piles of rocks, and all day, he's supposed to pick up rocks and take them to the other pile... and back again, and back, again, and again. Even though it's psychologically edgy, he is able to get the man who offered the advice on the train into the job, because he realizes that it isn't physically dangerous. This man, Horst, does have a pink triangle on his shirt. The longer they work together, across many months, these two men fall in love. Never touching, never looking each other in the eye. One day while working, they stand next to each other, again, never touching, and never looking, vocalize a sexual relationship, and verbally-- like phone sex-- make love. They both get sick. Yellow star Max is given medicine, pink triangle Hans is denied it.
You knew this would happen, what's coming....
One day, they're working and the guards come up to Max and ask how the medicine is working. Horst is coughing, hoping that they will hear and also get him medicine. They tell him to shut up, make a snide comment about putting an animal down. "Juede, come with us." They take them both to ten feet from the outer fence, take Horst's cap and throw it on the fence, and tell him to go get it. He charges one of them, and they shoot him down. They laugh and curse and walk off and tell Max to clean up the body. He is dragging him over to a mass grave, holding him by his armpits, and he's talking to Horst. Earlier in the movie, Horst was telling Max how he had felt enough pain, and he only wanted to be treated kindly and touched softly. After burying him and saying his goodbyes, he runs at the electric fence and kills himself.
No fucking joke.
"All Time" is a tough category... but off the top of my head, I'd pick Blue Valentine. Not the saddest, but definitely one of my favorites.