I new a lot of Dead Heads back in college, and traveled in the same circles, but I never got it, either. However, I still gravitate to the great artists, while also enjoying listening to all manner of new music, because I find you never know when or where you are going to come across that next great artist.
And the really good stuff in my experience continues to yield insights years on. In that class, I place Bowie, Miles, The Beatles, Bauhaus, early Talking Heads, Coltrane, and of course Radiohead.
Oddly, as time goes on, the more I hear the Stones, the less I hear in it.
The really important part of this, though, is that you have to be willing to reflect on the art, not just experience it. Without conscious reflection and attention, there is no opportunity to deeper understanding.
(And the last Dead show we attended we left after Little Feat, the opener. If any of the fans climbing the fences could comprehend that we were abandoning our ticketed rights before Jerry hit the stage, they would have died right there.)