6. Kris Kristofferson ($160 million)
Kristofferson enjoyed a brilliant career as a performer and singer-songwriter. He wrote some great hits for other artists, including Help Me Make It Through the Night and For the Good Times.
In 1985, Kris Kristofferson joined Johnny Cash, Willie Nelson, and Waylon Jennings to form a country group called The Highwaymen. He was inducted into the Country Music Hall of Fame in 2004.
As well as being a singer, Kristofferson has played many roles as an actor. He even won a Golden Globe for Best Actor in 1976 for his role in A Star Is Born, where he played opposite Barbara Streisand.