As I think about it, I actually do have some more thoughts on Paul Simon and Graceland, as I sit here finishing up some work (being a lawyer rules!) before I go out and the album plays in the background.
There's something that amuses me about our generation's recent re-appraisal/appreciation for Graceland (Vampire Weekend, obv, but also other bands now not being embarassed to namecheck the album, including, if I recall, Travis Morrison from Dismemberment Plan in an interview a couple years ago, et al). For people who are our age (that is mid-late twenties/early thirties), Graceland came out when we were at the perfect age to sort of passively and subconsciously absorb music that was being played by our parents (1986). Though everyone goes through a period where the music they want to listen to is the exact opposite of what their parents listen to, I have a feeling that many of us retain an affection for stuff we listened to as kids before we really had the opportunity to form our own taste. Although I can now listen to Graceland and appreciate the fluidity of the playing, the seamless integration of genres, and the effortless-seeming hooks, etc, when I was a kid I just loved the horn riff from "You Can Call Me Al."
I feel the same way about lots of things-- movies I loved as a kid will always make me happier than any movie I saw later and think is objectively "better" (Back to the Future-4-Life). And with other types of music-- as a kid, I was exposed through a variety of means to a handful of musicals, the cast albums to which are still some of my favorite music ever. While I generally have a soft spot for watching (and sometimes performing) musical theater, I'll never enjoy the ones I see now as much as the ones I saw/committed to memory back then. So, while I love Pirates of Penzance because I watched the Kevin Kline/Linda Ronstadt*/Angela Lansbury movie version literally hundreds of times, I've never seen HMS Pinafore and I can't imagine I'd like it that much. And for that matter, while I appreciate other Paul Simon albums (and actually grew up in a similar way with the Simon & Garfunkel albums, though at a slightly older age), I don't get nearly as much joy from them as I get from Graceland.
I wonder if there are any other pieces of culture (musical in particular) that were as ubiquitous and widely acclaimed as Graceland was at the time that can/will be re-appraised by our generation because we basically have an almost Pavlovian response to it.
*Incidentally that was another gateway into Graceland for me-- I already knew Linda Ronstadt as "Mabel" so I was really psyched to hear her duetting on "Under African Skies."