Kris Kristofferson – 84
It’s an unwritten rule to be a triple threat in Hollywood to make it through the decades, and that’s how Kris Kristofferson has managed to stand the test of time. The 82-year-old singer-songwriter and actor has recorded as well as written several hits, including Me and Bobby McGee, Comin Down, and Sunday Mornin.
His screen roles included appearances in Alice Doesn’t Live Here Anymore and A Star Is Born for which he earned a Best Actor Golden Globe. While Kristofferson continues working, he has dealt with multiple health issues over the past decades such as a Lyme Disease diagnosis.