Barbi Benton, 68 – $20M
Barbi Benton is a former model and actress, known for being a Playboy magazine star and a long-time girlfriend of the late Hugh Hefner. Barbi had a recurring role in the TV show Hee Haw, but aside from being an actress, she was also a singer, releasing a number of fairly successful albums until she retired back in the ‘80s. This was after getting married to George Gradow when she decided to dedicate her time entirely to raising her family. Since Hefner’s passing, Barbi has made several public declarations, rejecting the idea of turning the iconic Playboy Mansion into a museum.