Ah yes. I suggest this is the essence of regret ie remembrance of one's youth and the piece of you that has died with the artist, with a reminder of your own mortality. Rather that the death of an artist who ceased to be significant, say, 50 years ago.
So when, say, Bob Dylan dies nobody will regret that he isn't releasing awful Frank Sinatra pastiche records any more but they might still remember the first time they heard Like A Rolling Stone.