Hugh Hefner's Many Exes

Barbi Benton
Beauty Barbi Benton became Hefner’s main squeeze in the late ‘60s after meeting him while working as a model on his TV show “Playboy After Dark,” when Benton was just 18 and the magazine publisher was 42. Benton eventually released a few country music albums, starred in iconic TV series “Hee-Haw,” and appeared on the cover of Playboy a whopping four times, including in 1982, six years after she and Hef broke up.

Barbi Benton
Beauty Barbi Benton became Hefner’s main squeeze in the late ‘60s after meeting him while working as a model on his TV show “Playboy After Dark,” when Benton was just 18 and the magazine publisher was 42. Benton eventually released a few country music albums, starred in iconic TV series “Hee-Haw,” and appeared on the cover of Playboy a whopping four times, including in 1982, six years after she and Hef broke up.