But when a teenage extra named Barbara Klein started "acting" like Hef's girlfriend during episodes of the series "Playboy After Dark," she soon found herself cast in the real-life role, too.
Her new beau suggested she change her name to Barbi Benton, and a '70s pop-culture icon was born.
Not that it's unexpected, but some of the gorgeous women on Hugh's arm have been caught on celebrity sex tapes with other high-profile men.
Kendra Wilkinson, for example, is high on the list of celeb sex tapes and is no stranger to the attention.
Then again, maybe Hef's still pining away for his former steadies, "The Girls Next Door": Holly Madison, Bridget Marquardt, and Kendra Wilkinson. But at age 83, Hef has shown us time and time again that he's good at loving the ladies and then moving on.
Take a look at some of the women he's wooed over the years.
She wanted spontaneity—maybe a "quiet dinner together" or a visit to a "piano bar—and time away from the prying eyes of guests. I'd say I want to go to bed and get up at and work out. He doesn't like to be alone." story: Tuesday nights, family time with Conrad and the boys.
Honestly, if you look quickly at a photo of Hef's latest batch of ladies, it's even a bit hard to distinguish 22-year-old Crystal Harris from the 19-year-old Shannon sisters.
She was also involved in a very public relationship with illusionist Criss Angel.
In 2013, Holly’s personal dreams came true when she and her then fiancé Pasquale Rotella welcomed their first child Rainbow Aurora lasted just one season.
While the relationship between Hef and his ladies is dramatically different from the plural relationships we have grown accustomed to seeing ( After running circles with the commitment-phobic Hefner for years, Holly decided to call their relationship quits.
broke the mold with this hit reality series that helped pave the way for plural relationships to become a part of mainstream media.