The ending of Terranigma made me cry. Only time I've cried of sadness, IIRC.

Nothing beats Disney's "A Christmas Carol" (the one with Scrooge McDuck, Donald and Mickey) though, I can barely watch the graveyard scene.

I have a couple times. First time was when Rydia came back in the underworld and saved teh gang from Gobez(guess that was more from being happy). Another time shortly after would be when Cid jumps off the Airship to use a bomb and cover up the entrance to the underworld. I was like 10 I think when this happened give or take a year.

Eternal Sonata, when Polka jumps from the cliff and Retto goes own on his knees and is all like "Polkaaaaaaaaa!".

i had been watery-eyed for a couple of minutes, but that tipped me over the edge. Gawd, they were such a friggin cute couple.

in fact, loads of cutscenes from that game. wow.

I broke down in tears when I saw mario's star friend sacrificing itself for the super nova. Looking at mario's expression caught my eye.

Out of anger as a kid, yes.

Never.

I have never cried because of a game, movie or book. Both books and movies have made me sad but never close to crying. I honestly think the last time I cried was when I was 7 or 8.

I think its more something to do with me than anything else. When I heard my cousin died last summer I didn't cry either.

I don't think it has anything to do with trying to be manly. I just have this really weird ability of being able to emotionally detach myself from things around me when I have to. It can make me seem ruthless or uncaring sometimes.

lololololol

No. Nor a movie.

But I was that close to cry on the finale of Six Feet Under. But I didn't!

I guess that's just not how I express my feelings. That's why I have a brother.

SotC, SMG, FFIX, ME2, UC2, Okami all got me teary at the end just cause it was a breathtaking experience. There are more around but I can't think of them off the top of my head. I really enjoyed MGS4 but it definitely didn't get any sort of reaction like that from me. Heavy Rain had a couple moments within the story that got me revved up, but not really the end so much. It definitely connected me with the characters better than most movies though, but that's often true for me in adventureish games. LO made me well up in the scene at the end of the first disc.

Oh, and Phoenix Wright: Ace Attorney - Trials and Tribulations made me cry at the end in happiness, but not sobbing. Definitely had tears running down my cheeks and red eyes for the rest the night though.

In other media:

A good few times I've welled up reading. Ender's Game, a couple of Terry Pratchet books, Dragonriders of Pern on more than one occassion, Hitchiker's Guide series a couple times (yeah, sounds weird I know, but it's true), and teary from happy endings in numerous books. 

Plenty of movies make me teary. Up, as has already been mentioned, got me about ready to break down in front of a girl I had just started dating at the time.

In TV, a couple moments in Supernatural got me a bit teary. The end of Dollhouse made me cry a little, as did the movie Serenity (which was really the end of the TV show Firefly). I was about KO'd when David Tennant's Doctor Who died at the end of the last episode. No Doctor will ever replace him for me. :(

In anime Clannad After Story was a fucking bitch on the eyes. I outright cried twice in that, and got teary god knows how many other times. Probably the only thing I've come close to literally sobbing at in 10 years. Toradora got me teary at the end, as did Planetes. Kino's Journey never made me cry, but ripped my heart out nonetheless. The very first episode of Cross Game made me cry. Other anime have effected me emotionally pretty strongly as well, but I won't name all of them.

Most of these instances are more me getting teary or welling up a bit. I don't outright cry very often. Clannad, however... I mean this scene was just fucking cruel (warning don't watch if you ever plan to watch the Clannad series):

Dude...I am a crybaby when it comes to games:

Lost Odyssey - Several Times

MGS4 - After 10 years, finally playing the last chapter brought tears to my eyes. Also several times.

FFX, VI, VII and every other FF.