I enjoy a good cry to music, I actually seek it out sometimes. One of my buddies asked me once 'are you going to stay at home this afternoon drinking bourbon and crying to Gram Parsons?' and he was actually right. I tell people 'I won't be coming out this Saturday, I plan on listening to music and crying'.
So with that thought in mind, one of my favorite blubbing songs is '$1000 Dollar Wedding' by Gram Parsons. The bit where he starts singing about the Reverend Doctor William Grace is the 'oh fuck, it's coming' part. And then when he gets to the 'Where's the flowers for my girl?' bit, that's when I bust out crying.
Segue: how fucking great are Emmylou and James Burton? Incredible.