Kris Kristofferson – $160 million
Greatest Hits: Sunday Mornin’ Comin’ Down, Me and Bobby McGee
Kris Kristofferson enjoyed a marvelous career as a singer-songwriter and performer. The man wrote plenty of hits for his counterparts, and would collaborate frequently with Shel Silverstein. The Highwaymen was a supergroup made up of Kristofferson, Johnny Cash, Waylon Jennings, and Willie Nelson. He also acted in plenty of films, such as Blade, Alice Doesn’t Live Here Anymore, Heaven’s Gate, and A Star is Born. His part in A Star is Born earned him a Golden Globe. In modern times, Kristofferson has a home in Maui, Hawaii.
Kris Kristofferson
Paul McCartney – $1.2 billion
Greatest Hits: Yesterday
John Lennon could only be surpassed by a fellow former Beatle, Paul McCartney. His songs have been covered by more than 2,200 artists, with Yesterday being one of the most frequently borrowed. He was twice inducted into the Rock ‘n Roll Hall of Fame, as a solo artist and as a member of The Beatles. 1965 saw the leading stars being called MOB. Paul is also a knight, an honor that he received in 1997.
Paul McCartney
