Well, this will sound a little weird, but I'll post it anyway. Bob Weir and the entire Grateful Dead are on my mind.
I'm an emotional guy, and I'm not ashamed of it.
I have a friend who is not an emotional guy.
We were having a deep phone conversation one time, talking a bout a particular Dead show that we attended. We didn't know each other at the time of the show.
He said...I have to tell you something, and I hope you don't think poorly of me. I asked him what it was and he told me he had to leave the show because he started crying during it. He said something triggered him and he was bawling like a baby.
I just laughed at him and said why the fuck would I think poorly of you?
And he said...men aren't supposed to cry, and I was embarrassed. I said get the fuck out of here with that shit. I asked him if he was depressed when he was at the show. He said no, he was happy. I asked him what drugs he took, he told me he was dead nuts sober.
So I told him that I've cried at concerts before, and it is because you hear something in the music that triggers an emotion. That's all it is. Don't worry about it. Then I laughingly told him he is still an asshole, but knowing that you cry makes you less of an asshole in my eyes.
I was reminded of this conversation last night when I watched this reaction video. The guy in the video is a rapper, and he had no idea what the Grateful Dead sounded like, or what they were about. But if you watch the video, you find that he slowly gets it. I love watching his facial expressions, because he understands music, even though he never heard the Grateful Dead in his life. It's fascinating to watch it slowly click for this guy, and how blown away he gets.
That's how it was for me with this band. I heard the "it" that many people don't hear. That many people mock. Thinking this is some kind of weird ass hippie music or something, rather then some of the best muscians in the world, and that is what they indeed/are were.
It's the same reason people cry at operas. I don't cry at operas, but some people do, and I understand why.
The guy in the video doesn't burst into tears, but almost. I find stuff like this fascinating...because I can literally feel what he is feeling, and this band has been giving me goosebumps for about 55 years. And I've been getting mocked for it for 55 years too. I don't care. I hear something that rattles my soul with this band...that motivates me. That picks me up and carries me.
I wish I was friends with this guy in the video. Rest in peace, Bobby Weir.
= new reply since forum marked as read
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 