Most Depressing/Sad Movies, Shows, Anime, etc?

(Hitting you with the best anime would be Hunter X Hunter 2011) But if you want something emotional, then it was probably Ookami Kodomo no Ame to Yuki for me

Anime: Bokurano

Kids playing a hell of a "game", worth a try

me as a dude the only movie i watched that made me drop some tears is seven pounds.

Play Bad Rats, I assure you you'll be depressed/sad.

I counter you with movies that will make you cry out of joy, and yes, they quite literally do that. Not shitting you. Anyways,

• Sunrise - A Song Of two Humans - silent film from that Murnau guy who brought us Nosferatu, for some reason the church scene and the ending is a bit heavy. It might be a silent one, but it speaks more than any words. Oh boy I'm so meta now.
• It's A Wonderful Life - I know, it's a classic, but here in Hungary they never played it on Christmas on any TV channels, ever, so it's kinda rare to find someone who's seen it. In that way, it can hit so goddamn hard.
• Crash - not the David Cronenberg one, the other one from 2004 I think. Just make it to the "invisible bulletproof blanket" part and try not to brawl like a baby.
• City Lights (Charles Chaplin) - God Fucking Dammit Chaplin, you're supposed to make me laugh >:(

Grave of the fireflies

And i can recommend Clannad, too

Watch the great first season of The Walking Dead and then watch the second one. ;)

Clannad

Wolf's Rain, if you can get into the story. A little bittersweet but with a lasting whiff of melancholy.
While the writing is often sloppy, you can't beat the melodrama in a typical popular Visual Novel.

I just recently decided to finally give the original Tsukihime VN a shot, and holy jeebus did the story grab me by the balls. Like I said, the writing is often sloppy but the plot elements can take you off-guard, and while it can be a bit over melodramatic, I can't deny it can have a real effect once you're invested in the characters. Tsukihime has an especially strange mix of peaceful melancholy and emotional struggle. Trying to summarise it as a "vampire story" would be oversimplifying it, more a "modern paranormal drama" perhaps?

Then there was my first VN : "Saya no Uta".
A better title might have been "Putting the 'love' back into Lovecraft", haha.
It was weird as hell and there were only a handful of choices to make in the entire game, but it was worth it. I opened it with the intention of "Only playing a little, to find out how these VN things are". Next thing I knew it was about 5am and I had just completed it. No absolute protagonist, and really made me want to root for both the good and the bad guys almost equally.

Just be careful, though. If you don't look up a little of each VN before you play it, you will likely find that random sex-scenes appear out of nowhere (often feeling pretty tacked-on or unnecessary). Worse still is that rape in VNs seems to be a fairly commonly visited subject (though in my experience it is rarely glorified, but still used as a cheap-shot to get a quick, negative emotional response).

Dancer in the Dark is by far the most depressing movie I've ever seen, along with Synechdoche, New York

If you feel like absolutely hating your life for a couple of hours then there's nothing better than watching these.

Antonia's Line

Coyboy Bebop made me cry

brave heart
i cry every tiem when i watch the end

anime ano hana

Hmm...

As for game: Bastion was kinda sad. And Deus Ex: Human Revolution gave me this "feeling" that u get after finishing game that has good story. Its hard to explain but lets say that if my reaction after finishing eg. Call of Duty: MW 1-2 or another Crysis was "meh" than my reaction after finishing Deus Ex: HR was "damn...that was good"

Anime: Maybe not sad and depressing but Jormungand gave me few things to think over

Hotaru no haka (aka Grave Of The Fireflies) is the only anime ever that made my eyes wet, and it's probably mentioned loads of times here already.

depressing movie: Tyrannosaur

The Man Who Wasn't There and Atonement come to mind.

Games: Spec Ops TL, Bastion (lonely), BioShock Infinite (ending), and Heavy Rain (most depressing game intro EVER).
TV: Cowboy Bebop (dat ending ;-( "Bang"), and of course the demise of Captin Murphy in Sealab.
Book: The Curious Incident of the Dog in the Night-Time.

Movies: Casablanca, Wild Strawberries, Bicycle Thieves, The Deer Hunter.

Go for these, it's just what you want.

Oh, and if you want a good book, "Crime and Punishment" is the best book I've ever read. It's my favorite. It's deep and depressing. You should take a look.

The end of Metal Gear Solid 3 is kinda sad

Anime;

Monster. Its a slow burn, a bit like the Fugitive, but when the pieces fall into place.. Damn..
Full Metal Alchemist. Now hold on, let me explain :). On the surface it seems like any other shounen anime, but it has some real big/adult themes running through it. Some intense/sad moments in this one.
Grave of the Fireflies. Beautiful, but sad. But beautiful. Sad.
5 Centimeters Per Second. Me likes.
Cowboy Bebop if only for the ending.

Movies;

Donnie Darko. Is there a better movie? Maybe Leon.. (Watch the short version!!)
Leon (The Professional) Is there a better movie? Maybe Donnie Darko. (Watch the short version!!)
Requiem for a Dream; Freaky, but beautiful. Haunting.
Eternal Sunshine of the Spotless Mind. Is that water coming out of my eyes? Heartbroken.

Games;

Spec Ops: The Line was the most recent game that opened my eyes a bit. Seemed really generic, but ive seen stuff in that game that ive never seen done before in my 20 years of gaming. Amazing stuff where sometimes dying is a good thing.

Mirai Nikki

Boku no Piko

anime :Kimi ga Nozomu Eien

Lilja 4-Ever NOT FOR CHILDREN u will remember this movie FOREVER

The Hunt this movie will leave u frustrated and and angry as hell

neither of these movies are for children and they are from real life not made up fantasy shit; these movies are not for everybody - even adults. From the right perspective these movies are very educational.