times. Usually it's because of the connection to some tough time in life. That means rough breakups usually (I've had a lot of those), but also people who've passed, or times I was deep into the bottle (or some worse thing) trying to climb out, and the song was there for me at the time, speaking truth, but other times it's just the universality of the sentiments, expressed beautifully. Sometimes I cry cause they make me happy, too.
I quite like the Dead too but I can't say any of their songs are in that list, for me their songs in general don't seem to be out to deliver an emotional gut punch. Plus when I listen to them it's usually the musicianship that commands my attention. I don't mean their songs never have emotional heft, for example Touch Of Grey has made my eyes well up once or twice when I was feeling old, but to me they're more of a "good times" band. But by no means have I heard every song of theirs, so there's that.
Anyways, music makes my eyes well up pretty often, and rather than thinking of them as "depressing songs" like some people I've played them for do, I treasure the songs that do that to me, they're some of my all-time favorites. And I don't trust people who say no song/music has ever brought 'em to tears 
Cheers Lucky 
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