Id have to say Threads is the saddest film Ive ever seen
When a Man loves a Woman
Moonlight and Valentino
Playing by Heart
Yes! to Boys on the Side
Trees Lounge
Once again, I supply my backing for Grave of the Fireflies
However, I cried after finishing Love Hina. I was sad that I didn’t get to see any more 
I agree with you wholehartedly, I was unnable to think straight for days after watching it, and I haven’t been able to see it again ever since. I just left me feeling terrible and I shudder everytime one of Selma’s songs comes up on the radio.
Saddest and most depressing, but good.
Beaches.
Mask (the Cher one, not Jim Carrey’s “The Mask”) is also very sad.
Grave of the Fireflies, no question.
I’m a grown man and I started crying five minutes in and was unable to stop until the end.
[Spoiler – although not really because this all happens right at the beginning.]
For those who haven’t seen it – it’s the story of two Japanese war orphans slowly starving to death. It starts with the death of the older brother in a busy train station. When workers carry his body out they find a battered candy tin. They throw the tin out into a nearby field and it comes open, scattering the ashes it contains, the ashes of the boy’s little sister. The ghost of the little sister appears, and the boy’s ghost joins her. The rest of the movie is told in flashback, showing how two regular kids from a loving household can wind up dying abandoned and alone.
For a guaranteed few tears at the end I’ll vote for My Dog Skip. Anyone who’s grown-up and loved a dog (and most everyone else besides) cannot keep a dry eye for this one. I’ve seen grown, tough-guy men’s men hiding watery eyes after this. Maybe not the most poignant film ever but bittersweet.
Dancer in The Dark
Solaris (original Tarkovsky version, 1971)
Vivre sa Vie
The Unbearable Lightness of Being
As a child, Bambi was probably the saddest film my unsuspecting parents ever took me to see. I can still remember a theater full of crying children with a lot of parents muttering nasty things about Uncle Walt.
Old Yeller was another Disney chuckle-a-thon.
Then there was Dumbo’s mom…
hmmm.
Makes me wonder just what kind of sadist was Uncle Walt?
I have had an unviewed DVD of Dancer in the Dark since September and I am very, very afraid to watch it.
The Joy Luck Club gets me bawling almost all the way though it.
I’ll second the vote for “Threads” though it was more along the lines of just horribly depressing than sad.
Waterworks wise, without a doubt In the Name of the Father.
This is the only film to literally bring tears to my eyes as an adult. I had been holding it in, but the final scene when the freed Daniel Day-Lewis announces on the Court steps that (IIRC) “I will fight on, in the name of my father” broke the seals.
milo
Another vote for My Dog Skip…
also Terms(tears) of Endearment;)
Kazaam.
“Truly, Madly, Deeply”
They just love each other so much.
Whistlepig, who will now be walking around for the next two days with his brain going:
[Bill Murray in “Stripes”]
OK, who here cried when Old Yeller died? Huh? C’mon, you know you did. Raise your hand if you cried. That’s right, we all did."
[Bill Murray in “Stripes”]
The Last American Virgin
I actually felt sorry for Gary at the end of that movie.
Stepmom!! (No, Please leave the WHOLE box of kleenex)
I would also have to agree with the vote for Beaches!
I have never told this to a living soul.
When I was twelve I saw Silent Running on TV. I sat up all night crying my eyes out.
In more recent times:
Chasing Amy
American History X
both affected me profoundly, for different reasons of course.
It’s a little bit obscure, but the movie Miracle Mile with Anthony Edwards and Mare Winningham has got to have one of the most crushingly sad/depressing endings I’ve ever seen
Chris W