Barbie Benton

Seen here with his then girlfriend Barbi Benton, a multi-faceted talent known for her comedic skills, as well as obvious modelling prowess. These two love-birds dated for over a decade until their relationship took a drastic turn. Barbi Benton was looking for something more solidified with Hefner, and by all accounts Hefner regretted not marrying her, but ultimately Benton fell head over heals for tycoon George Gradow, who she would marry. Hefner’s top bunny for several years, was widely considered as the most beautiful woman of her era, and we can only assume Hefner had a few regrets with how the relationship ended, but we’re also guessing he didn’t have to wait very long to fill the void.