From His First Wife to the Girls Next Door: The Many Loves of Hugh Hefner
Hefner met longtime love Benton, 24 years his junior, on the set of his TV show, Playboy After Dark. The pair traveled the globe in the 1970s before moving West to Los Angeles; she went on to appear on three Playboy covers and in two spreads. "I only regret not marrying Barbi because it finally led to our going separate ways," Hugh told PEOPLE in 1980. "But I have been married and have children and wasn't, am not, interested in doing it again. Barbi hadn't had that and wanted it."
That first go-round for Hef was with wife Mildred Williams, a Northwestern University student he married in 1949. According to The Hollywood Reporter, Williams cheated on Hefner prior to the pair's wedding day, so allowed for an open marriage during her 10 years with Hef. Despite the unconventional setup, they had two children: daughter Christie and son David.
Next up in the early 1980s was 20-something Tweed, a Canadian model and actress who had a role on the CBS nighttime soap Falcon Crest when the two got together. "He's got a real special feeling for this one," a friend told PEOPLE in 1982. "She's bright, beautiful, and big," That didn't mean marriage was on Hef's mind. "When Shannon says 'Why don't we get married?' and I say no, she punches me," Hef told PEOPLE. "I think having kids is a reason for getting married. I've had two." Shannon professed understanding. "Marriage is not natural for Hef," she explained. "It's natural for me to think in those terms since it's the first time I've known it's right. But it's going to take him longer, since he's been through it before."
Leigh was one of many young Playmates Hefner dated, living with him for several years in the 1980s. However, their split was not without drama: she filed three lawsuits against him, including a $5 million palimony suit in 1988. "He promised to marry me, he promised to have a child with me, promised to support me," she said in a press conference that year. Hefner denied the charges and said he did take care of her, moving her into the Mansion and giving her a hearty allowance. "This is not a palimony suit, it’s a publicity stunt," he said. Leigh later went on to call the Playboy inner circle "almost like a cult. You start forgetting who you are and what you believe is right."
Hefner did give marriage another try, though, this time with 26-year-old Conrad, whom he wed in 1989 after they met at a Playboy shoot two years prior. Together they had two sons, Marston (pictured) and Cooper, but after nearly nine years of marriage, they announced their split (though the divorce wans't finalized for nearly 20 years).
"Kimberly is the love of my life, but there was a growing difference in terms of interest," Hefner told PEOPLE at the time. "I love Hef deeply," she added. "But we're on different schedules. Sometimes you want to go downstairs and have quiet, as opposed to running into 50 people. I just wanted a change." She moved into a $7 million spread next door to the Playboy Mansion, bringing the couple's young sons with her.
MANDY & SANDY BENTLEY
In the late '90s/early 2000s, Hef mended his heart with college students and twins Sandy and Mandy Bentley, then 21. At 73, he admitted to using Viagra: "I'm dating twins, I have to," he joked.
Around that same time, actress Roderick was in the picture — as were a handful of other girls. "When I came out of the marriage, I was emotionally beat up and bruised. But I discovered beyond my wildest dreams that a whole generation of women wanted to come out and play," he told the U.K.'s Telegraph. For nearly three years he dated Mandy, Sandy and Brande; when Brande moved to Hawaii to shoot Baywatch Hawaii, "the concept was the same but the number changed," Hefner said of his paramours. "It went up to six, seven."
TINA MARIE JORDAN
One of those "six, seven," was Jordan, whom Hefner dated in the early 2000s. He made her Playmate of the Month in March 2002.
BRIDGET MARQUARDT, HOLLY MADISON & KENDRA WILKINSON
Perhaps Hefner's most famous girlfriends, Wilkinson, Marquardt and Madison were the stars of his reality show The Girls Next Door, which centered on the trio's relationship with Hef and their glamorous lives inside the Playboy Mansion. The show was a hit, airing on E! from 2005 to 2010, and made stars of its three female leads while introducing a new generation to Hef.
It wasn't without its dramatic moments, though, and after the series ended, Wilkinson and Madison both wrote memoirs about the mixed feelings they had while dating Hefner.
KRISTINA & KARISSA SHANNON
After Wilkinson, Marquardt and Madison moved on, Hefner briefly dated the Playmates and twins (they appeared on the final season of The Girls Next Door, too). But per an interview on the show, Karissa explained the twins' relationship with Hef was more "for fun," less for romance.
Hefner's final love was Playmate Harris, whom he wed on New Year's Eve 2012. The two — who had a 60-year age difference — became engaged in 2010, though Harris left Hefner four days before their planned June 2011 wedding. The two reconciled in 2012, and set a new date after Hefner's divorce from Conrad was finalized. "We really complement one another, we have a wonderful time together, and I love her," Hefner told PEOPLE.