It feels great. It's called culture, and being aware of it, not a blind consumer of what tastes good (McDonalds tastes good too).
>there are no absolutes in music (as an art form)
No, but human culture has, and always had, a way to prfioritize what's important and what's not besides mere consumption or influence (crap has also influenced a lot of imitators).
>Dylan himself probably never thought he'd be as important a musician as his heroes - Elvis, Little Richard, etc. but now they are all in the same conversation.
That's irrelevant though, because it's not the artist that determines their own worth but their work, its quality, and its cultural impact.
>music is fun. the expected almost never happens.
Except with TSwift, Diplo and co songs. Where it almost always happens.