His studio stuff can sound awful, though I've always liked Dancing in the Dark.
One album missing from the list here is the Miles Davis album 'Kind of Blue', the album that those who want to make out that they know jazz say is amazing even though it's probably the only jazz album they know and they have nothing to compare it to.
Anyway as far as the idea of when I listen to albums like these the answer is not very often. I like discovering new stuff (whether recent or old) so I spend most of my time doing that than hearing things I already know.