The long list of hot women Hugh Hefner has slept with – #2 will shock you! (With Pictures)

3. Barbi Benton

Barbi Benton began her Playboy career when she was 18 as co-host of the entertainment show Playboy After Darkalongside Hugh Hefner. He asked her for a date while currently 42, but this didn’t deter Benton. They were together for several years during the Playboy hay days, meaning she was very prominent in the company during her time with Hefner.

She went on to cover the magazine four times: July 1969, March 1970, May 1972, December 1985, but never achieved a Playmate of the Month title. Other accomplishments include television appearances, work as a country singer, and movie appearances as both a guest and an actress.