Kris Kristofferson – 86
Kris Kristofferson is a talented songwriter, and among the several hit songs which he wrote were Sunday Mornin’ Comin’ Down and Help Me Make It Through the Night. He has an amazing career as a solo singer, but he also became popular for being part of the group called The Highwaymen. Aside from music, he was also successful in acting. Many of you might remember him for the award-winning performance he had had in the original A Star Is Born movie back in 1976. Kristofferson hasn’t entered retirement yet as of today, and his most recent role was in Blaze back in 2018.