Not many songs make me want to cry, but
Johnny Cash's version of Hurt gets me every time. I think it's because it reminds me of my dad and all the shit he's caused in my life. I don't know. Very emotional track, not something I listen to frequently. I do like it though.
I can't recall most of the movies/TV series that have made me weep, but I'm sure there's quite a lot of those. Like with many others it seems, Jurassic Bark and Luck of the Fryrish definitely made me tear up a bit. I also remember seeing an episode of The Simpsons where Homer eats some poisonous fish(?) and stays up all night waiting to die, that was some heavy stuff for a young me. Also that one The Fresh Prince of Bel-Air episode where Will's father shows up, but takes off again and Will says "how come he don't want me, man?" - or something along the lines - to Uncle Phil, shit, that made me bawl.
Can't remember too many video games that have made me cry, but Batman: Arkham City's credits almost made me tear up.