BARBI BENTON – $20 MILLION

Barbi Benton began her professional investments as a model and was only 18 years old when she was given a chance to appear in Hugh Hefner’s magazine. She participated in a presentation as a stand-in model. Hefner, also the show’s creator, supported her, and she eventually rose to the position of co-host. She also appeared frequently on the comedy series Hee Haw for four seasons as a featured singer.

Her single, Brass Buckles, peaked at #5 on the Billboard country singles chart in 1975. The following year, Benton released her debut album, Barbi Doll, which peaked at #17 on the US chart. She married the businessman and retailer George Gradow in 1979, and the two have been happily married ever since. After leaving the entertainment industry, she worked as an interior decorator and took care of her two kids.