Playboy founder Hugh Hefner died Wednesday of natural causes at the age of 91. The iconic publisher had his fair share of girlfriends and wives over the years, including actress and model Barbi Benton. Now 67, Benton met Hefner when she was an 18-year-old extra on “Playboy After Dark.” 

Born Barbara Klein, Benton changed her name at Hefner’s urging. She appeared on the cover of Playboy and inside the magazine, though she was never officially a Playboy Playmate or a Playboy Bunny. Her career consisted otherwise of movies like “Deathstalker” and television shows like “Hee Haw” and “The Love Boat.” 

Hefner was 42 when the pair started dating. She went on to appear on four Playboy covers and posed nude in the magazine.

“I was shy and would make the photographer turn his back when I changed poses,” Benton reportedly said of her photoshoots. “By the second one, I just let it all hang out.” 

GettyImages-2638834 Hugh Hefner and then-girlfriend Barbi Benton fly to London in 1970. Photo: Getty Images

Benton also used her real estate prowess to help Hefner find the property that became the now-iconic Playboy Mansion, according to Fox News. Her career in Hollywood, however, never exploded into stardom. 

“I kept making the wrong moves,” Benton told People magazine in 1980. 

Benton eventually met real estate developer George Gradow and married him in 1979. She became an interior decorator, and the pair had two children, Alexander and Ariana. 

“We’re so alike,” Benton told People. “George is a one-woman man, and I could never get beyond dating more than one man at a time.” 

The couple apparently did well for themselves: in 2011, they listed their 12,000 square foot home in Los Angeles for almost $12 million, according to Variety. Hefner and Benton remained friends even after they broke up. Benton has stayed out of the Hollywood spotlight for the most part. In 2014, however, she returned to the limelight for a brief moment to discuss allegations of sexual assault against Bill Cosby. 

“Bill Cosby was one of the first people I met at the mansion, shortly after I met Hef in 1968,” Benton told the Daily Mail. “It was unusual for a family man to be at the Mansion — especially as regularly as Cosby was.”

Benton went on to say that Cosby had what appeared to be a steady girlfriend at the Playboy Mansion and that she had not heard of any allegations of sexual misconduct at the time.

“I saw him there so many times I couldn’t count them,” said Benton. “He would come to be with this one particular girl — I am not going to name her, but I will say that her name has not come out in any of the recent accusations against Cosby. The relationship went on for a long time, well over a year.” 

GettyImages-617924282 Actress Barbi Benton arrives at the screening of Summit Entertainment's 'Hacksaw Ridge' at the Samuel Goldwyn Theater, Oct. 24, 2016 in Beverly Hills, California. Photo: Getty Images