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I second Requiem for a Dream, even if it wasn't so much sad as utterly bleak and brutal. The film is brilliant, but I can honestly only watch it maybe once a year.
Another one I'll add to my list is A Walk To Remember. Great movie, and Mandy Moore and Shane West were amazing in it, but the movie was heartbreaking.
Requiem For a Dream
Irreversible
Schindler's List
Hotel Rwanda
Steel Magnolias
Sophie's Choice
The Elephant Man
Torch Song Trilogy (funny and sad at once)
What Dreams May Come
.....many others I'm sure I'm forgetting. I'm a big softy when it comes to movies.
Never saw the whole thing.....but I heard the guy who made "My Life" with Micheal Keaton say he wanted it to be the "Terminator" of sad movies. Watched a few minutes of it and had to shut it off.
Untamed Heart
City of Angels
Saving Private Ryan
What Dreams May Come
Pan's Labryinth (the ending anyway)
Hero & House of Flying Daggers had their moments (and visually stunning to boot)
From my childhood...ET and Ol' Yeller
I own Requiem for a Dream. This one goes a bit beyond sad though, so I wouldn't include it on my list. It's kind of in a class by itself.
It starred Jimmy Stewart as a Father of a large Virginia family, who DID NOT want his family involved in The Civil War. I saw it with a group of airmen and I don't think there was a dry eye in the theater.
A lot of mine have been posted so I won't repeat them. I'd add one that has not been mentioned unless I missed it. Brian's Song is a made for TV movie from 1971 starring James Cann and Billy Dee Williams. A real tear jerker.
The saddest movie I've ever seen is American Psycho. Seeing the prostitute lying dead at the bottom of a stairwell after Christian Bale dropped a chainsaw on her from eight floors up after chasing her bare-ass naked through the darkened halls of an otherwise abandoned apartment building.
I may have answered this already, but in case I didn't...
1) Old Yeller (Still I cry)
2) The Champ (Another one still I cry)
3) Simon Birch (Haven't seen it in a long time, but bet money on me crying)
4) Shale Hands With the Devil. (when they kill the Prime Minister of Rwanda when she is on the phone with General Romeo Dallaire)
I know allot of people on the forum thing me to be some sort of Heartless Ass Hole, or simply a shit disturber (well the 2nd one is right anyway 😀). Truth is I am a big softy, who wears his heart on his sleeve. That is really why stuff can get me so riled up at times.
Anyway, if you haven't seen those movies, they'll get to ya.
ST
PS
I almost forgot, The Happy Wood Cutter is tragic... at least the 10 disc bootleg directer's cut special addition I picked up when I was in China Town last Wednesday.