I’ll put in a vote for someone who rarely makes these kinds of lists: Paul Simon. This guy is in his SIXTH decade of professional music, and has been a monster star since the 60’s. And unlike a lot of these other bands that haven’t done anything memorable for a long time and have stayed with the same formula, Simon keeps mutating from one form to another, always making it excellent. Folk, Gospel, Soul, Rock, Jazz, World Music, Country… And almost every album he puts out is critically acclaimed, very different from the last, and often spawns big hits.
And, he’s a good comedian and a member of the 5-timer’s club. That’s gotta be worth something.