Kris Kristofferson – 84 years old
American country singer-songwriter Kris Kristofferson is undoubtedly one of the most successful artists of all time with hits like Me and Bobby McGee, Sunday Mornin’ Comin’ Down, and countless others. He is also one of the few music artists who have enjoyed a successful career in Hollywood through the years, starring in movies like A Star is Born and Heaven’s Gate, and even winning a Golden Globe. He has a huge net worth pegged at approximately $160 million.