19. Phil Lesh (77)
Having released his first single at the age of 26, Phil Lesh went on to have an illustrative career spanning many decades with the Grateful Dead. There seems to be no stopping Lesh as he continues to tour with Bob Weir with their band Furthur. He released an album in 2002. While he scaled back his touring in 2014, he still plays the occasional gig as Phil Lesh & Friends whenever the thirst for music calls.