Hugh Hefner’s Girlfriends: Complete List And Pictures Of Playboy Founder’s Partners

Playboy founder Hugh Hefner died Wednesday at the age of 91 inside the Playboy Mansion in Los Angeles, California. Hefner had no shortage of girlfriends and wives during his tenure as one of the world's most notorious publishers.

Here's a look back at some of Hefner's most memorable relationships.

Barbi Benton

Barbi Benton, nee Barbara Klein, met Hefner when she was an 18-year-old extra on “Playboy After Dark.” Hefner was 42 at the time and encouraged her to change her name. 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 said of her photoshoots. “By the second one, I just let it all hang out.”

Shannon Tweed

Actress Shannon Tweed dated Hefner in 1982, the same year she was Playmate of the Year. Twenty-five years old at the time, Tweed starred on CBS soap opera “Falcon Crest.” Hefner was 56 at the time they dated.

“When Shannon says, ‘Why don’t we get married?’ and I say no, she punches me,” Hefner said at the time, according to People magazine. “I think having kids is a reason for getting married. I’ve had two.”

Mildred Williams

Williams was Hefner’s first wife: the pair married in 1949 and divorced in 1959. The couple met at a party after high school, though Hefner left soon after for the United States Army. Williams cheated on him while he was overseas, but they still married. Hefner and Williams had two children together: Christie, 64, and David, 62.

Kimberley Conrad

Kimberley Conrad was Hefner’s second wife: they married in 1989 and divorced in 2010. The pair had two children together: Marston Hefner, 27, and Cooper Hefner, 26. The model and actress was named Playmate of the Month in January 1988 and Playmate of the Year in 1999.

Holly Madison

Hefner and Madison met in 2001 during her tenure as a Playboy model. The two spent the night together and she moved into the Playboy Mansion soon after to become one of his many girlfriends. Madison and Hefner ended their relationship officially in 2008. She later published an expose on life in the Play Mansion called “Down the Rabbit Hole: Curious Adventures and Cautionary Tales from a Former Playboy Bunny.”

Kendra Wilkinson

Wilkinson met Hefner in 2004 at his 78th birthday party after she was hired to be a “painted girl” at the party, or a woman who appeared nude with painted on accessories. Wilkinson soon after moved into the Playboy Mansion and went on to star on the reality show “The Girls Next Door.”

“Hef changed my life,” Wilkinson told E! News Wednesday. “He made me the person I am today. I couldn’t be more thankful for our friendship and our time together. I will miss him so much but he will be in my heart forever.”

Bridget Marquardt

Marquardt, now 44, starred on “The Girls Next Door” alongside Madison and Wilkinson after moving into the Playboy Mansion in 2002. One of Hefner’s many girlfriends at the time, Marquardt appeared on the cover of Playboy in November 2005, September 2006 and March 2008.

“So sad but forever grateful for all the wonderful memories and amazing experiences #RIPHef #Playboy,” Marquardt tweeted Wednesday.

Crystal Harris

Harris was married to Hefner at the time of his death Wednesday. The couple met in 2008 and started dating in 2009. Named Playmate of the Month in December 2009 and donned the cover in July 2011 as “Mrs. Crystal Hefner.” Harris, 31, was more than 60 years younger than Hefner.

“I think the center of her life is us and you can’t ask for more than that,” Hefner told US Weekly in 2014. “With the age disparity, I’m a very lucky cat. I’m very, very happy.”