Hugh Hefner's Wives and Lovers Through the Years

Wed Jul 19 2023
By   tashi

Hugh Hefner married three of his famous girlfriends: The Playboy founder was a notorious lover!  

The name doesn't require an introduction but here's some anyway. Hugh Hefner's name could be a synonym for scandals. The infamous founder of Playboy magazine, and the equally hedonistic chain, The Playboy Club, died at 91, in 2017. Today, Hefner is remembered with the same taint with which he was associated when he was alive.  

Born Hugh Marston Hefner on April 9, 1926, in Chicago, he launched his magazine, Playboy, in 1953. The entertainment magazine, which he gradually spun into an entertainment giant, masqueraded as an emblem of the sexual revolution for decades, until the world saw it for what it really was. Hefner was accused of exploiting many women during his life span.  

Hugh Hefner's Three Marriages!  

The infamous philanderer walked down the aisle three times before his death in 2017. Hefner wasn't born the unconventional and hedonistic man that he is remembered as. There was a time when the Playboy founder had a normal life and was a one-woman man.   

Hugh Hefner was the founder of Playboy empire.
Hugh Hefner, the founder of Playboy, died at 91, in 2017. Photo Source: Instagram

Hugh's first wife, former Northwestern University student, Mildred ("Millie") Williams, is often blamed for turning the Hefner into a ladies' man. Hugh and Millie got married in 1949 and an alleged affair on his wife's part reportedly devasted Hefner. "I had literally saved myself for my wife, but after we had sex she told me that she'd had an affair," Hugh said about the ultimate betrayal.  

The couple welcomed two kids before splitting ways in 1959. During their 10-year-long nuptial, a disappointed and jaded Hefner cheated on his wife many times, and Millie, who was overwhelmed with her own guilt, endured the pain. Hefner continued his casanova lifestyle for decades and in 1989, he married his second wife, Kimberly Conrad, who was Playboy's playmate of the year in 1989.   

Hugh Hefner got married three times.
Hugh's first unfaithful wife allegedly devasted him. Photo Source: Instagram

Hefner's second nuptial at the age of 62 was a big deal and likewise, it drew massive attention. Hefner was once again a traditional man as Conrad's touch transformed his wandering ways and his infamous Playboy mansion. The couple together welcomed two sons. The couple called it quits in 1998 but remained nominally married until 2010.  

Hefner later claimed that he was a faithful husband to Conrad, who apparently cheated on Hugh. Hefner's way of getting over the divorce and his family falling apart was by dating multiple women at once. The porn king delved into his third marriage way quicker than his second.   

The Playboy founder married his last wife, Crystal Harris, in 2012!  

Hefner was 86 when he married his third wife, then-26-year-old Crystal Harris, on New Year's Eve in 2012. The duo's controversial marriage garnered much criticism for obvious reasons. The pair remained married until Hefner's death at 91. Crystal, 37, recently opened up about her marriage with Hugh.  

The former Playboy model pledged to unveil the truth in her upcoming memoir, Only Say Good Things. Speaking about her controversial alliance with the porn king, Crystal said, "My marriage to Hugh Hefner was very complicated It was one where, no matter how I was treated, I always felt like I had to protect him."  

Hugh Hefner's Girlfriends Through the Years!  

Hefner's polyamorous love life is a known fact by now. The late publisher certainly didn't flinch talking about his unconventional lifestyle. And once, Hefner even claimed to have slept with over 1000 women. The January 2022 A&E docuseries, Secrets of Playboy, explored the disgraced legend's life in his Playboy mansion.   

Hugh Hefner died in 2017.
Hugh claimed to have slept with more than 1000 women. Photo Source: Instagram

Among Hefner's myriad of lovers through the years, a little more than a dozen held a special place in the publisher's heart, and in the tabloids' slot. Hefner had numerous liaisons while he was married to his first wife, all of which went unrecorded. The Playboy founder's first notable girlfriend after his first divorce was Barbi Benton.  

Hefner pulled Barbi from obscurity and made her the cover star of his magazine many times, all while sharing a romantic relationship with the 24 year younger model. The duo's romance lasted until 1976. From 1976 to 1981, Hugh's most prominent arm candy was Sondra Theodore, who is now one of the main playboy mates to accuse Hefner of grooming her.  

Hugh Hefner had three children.
Hefner's many girlfriends have accused the late porn king of grooming and more. Photo Source: Instagram

The alluring divas, Shannon Tweed, and Carrie Leigh were with Hefner throughout the 80s. Leigh famously filed a lawsuit against the womanizer, accusing of him running a sex cult. "It's like the song ‘Hotel California–'Mirrors on the ceiling, pink champagne on ice," Leigh said of Hugh's vulgar business. 

Following his second failed marriage, the Playboy founder dated Brande Roderick, who wasn't necessarily the only woman in his life at a given point. Roderick seemingly shared a special relationship with the infamous philanderer as she had nothing but love for Hugh in her statement.  

"Hef was a wonderful person," Brandi said, adding, "I feel so sad that I even have to defend him because he's (was) such an amazing person." The late publisher was with television personality Holly Madison for seven years, from 2001 to 2008. Madison is one of the many who spoke against Hefner.   

Hugh Hefner famously dated Carrie Leigh.
Hefner is survived by his widow, Cyrstal, and his four kids. Photo Source: Instagram

Hefner's other girlfriend, Kendra Wilkinson, who gratified the porn king, from 2004 to 2008, is one more among a few who spoke well of Hugh. "Hef changed my life," Kendra said. She added, "he made me the person I am today."  

Hef's relationship with twins Kristina and Karissa Shannon also stands out from the rest. The aforementioned noteworthy names aside, the Playboy founder's dating history also includes Marilyn Cole, Lillian Muller, twins Mandy, and Sandy Bentley, and Izabella St. James. 

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