Kris Kristofferson, 82 – $160 million
Everyone knows the hits Me and Bobby McGee, For the Good Times, Help Me Make It Through the Night, etc. Kris Kristofferson is definitely one of the most famous country music singers and songwriters who were inducted into the Country Music Hall of Fame. Kristofferson released a new album in 2013 titled Feeling Mortal and another one in 2016 titled Cedar Creek Sessions which was nominated for a Grammy Award. He also appeared in a number of films and TV shows, most recently in the 2018 movie Blaze. He currently has about $160 million in the bank.