I will say the last movie I watched that made me cry recently is "Mary And Max".
Seriously, do what you have to to see this movie. It's adorable, but mature, no swearing, has a little questionable content, but it's wonderful. Get an account to Netflix and Instant Queue it if you have to. I watched this last week (as of this writing), and I was thinking I wasn't going to cry, but by the end, I cried. I kind of want to cry right now, just thinking about it. Don't look up small, individual scenes or anything, go find this movie. It made me cry where "Up" did not. True story, I did not cry during "Up".
The only video game to make me cry, short of "King Kong: The Video Game", for different reasons I won't explain, is "Earthbound". Earthbound made me cry because of the entire final act, for if nothing else, a major fight between what could be the equivalent of the Nothing from Neverending Story.
Also, the ending theme, "Smiles and Tears" makes me cry. I seriously can't listen to it with anybody singing right now. It makes me cry just listening to it. Of course, the instrumental version makes me do the same thing.