I used to cry over freaking everything when I was younger. Mostly because I had a huge temper problem, and I was one of those kids who always seemed to cry when he got angry (which would lead to people calling me a crybaby which made me even more angry, which in turn made me cry more; yes it was a vicious cycle). After I hit high school though, I learned to mostly bottle up my emotions. The last time I cried all out was SEVERAL years ago (in either 7th or 8th grade, I think; which would be about '05 or '06). I have come pretty close a couple times due to stress at college, maybe let loose a (manly) tear or two.
I think I teared up at a few movies I've seen over the past couple years as well, but I don't really count that, as I assume we're talking about more life related crying, and crying at a movie isn't really due to your own emotions, it's caused by an empathetic response to emotions or events in the movie.