Barbi Benton, 68 – $20 Million

Barbi Benton became popular during the ‘60s throughout the ‘70s as she appeared in the hit sitcom, Hee Haw. She also became a four-time Playboy magazine cover girl that gained her a worldwide fan base. Barbi was also the partner of Playboy founder Hugh Hefner for many years and she lived with him in his cool mansion.

Three years after her separation from Hugh, Barbi married George Gradow, which made her decide that she would have a semi-retirement to focus more on her family. Sadly, Barbi decided that it was finally a time to retire fully from the industry making her leave the limelight in 1986.