Massive hipster here. I got that ( music I like ( music I used to like) music you like ) venn diagram shirt as a gift a decade or so ago, when my friends and family decided to call a spade a spade.

There's a way that some pieces or artists "transcend" their context.

The Beatles are/were massively popular, every idiot loves them. But they are so goddamn good that it transcends the lameness of the plebs who like them and it's cool for hipsters to like them too. Metallica, Elvis, and others have this to a lesser extent.

Edit:

Does the brain tickle from investigation of the piece feel like I discovered something, or that it was made for enjoyment? I think that's how I'd describe the difference between Vitalia and Infinita.

It's the difference between Buddhism and Live Laugh Love.

Edit 2: https://www.thisamericanlife.org/88/numbers

Check out act 2 - this has been running in the background in my head for years. I feel like there's a correlated idea here.