In the course of his 91 year-long life, Hugh Hefner had quite a lot of companions. He was married three times and often dated more than one woman at once. It was all a part of his personal brand that is still lucrative today, four years after his passing.

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The beginnings of Hugh Hefner's love life date back to 1949 when he married his first wife. At the time, he was 23 years old. The OG Playboy was never again single. The infamous Playboy Mansion was filled with women much younger than him. Today, the once glamorous villa is abandoned and falling apart.

11 Wife #1: Mildred Williams

Hefner was married to Mildred Williams for ten years, but it wasn't his longest marriage. They met at the Northwestern University in Illinois and tied the knot soon after. According to Hefner's interview with the Daily Mail, Williams had cheated on him before they got married, which devastated him. "I had literally saved myself for my wife, but after we had sex she told me that she'd had an affair. That was the most devastating moment in my life," he said. The cheating scandal might explain why he did a complete 180 in his attitude towards romantic relationships. They got a divorce in 1959.

10 Barbara Lynn Klein

For the next decade, Hugh Hefner kept a low profile as far as his dating life went. In 1969, he started dating Barbara Lynn Klein, the first of many Playmates.

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They were together until 1976. During that time, Hefner convinced the twenty-something year old that she should change her name to Barbi Benton - and she did. Back then, working at the Playboy Mansion was said to be a good enough gig. Being a Playboy Bunny was a lucrative job.

9 Shannon Tweed

Shannon Lee Tweed Simmons is a Canadian actor that was at the forefront of making erotic thrillers. In 1982, she was named the Playmate of the Year and dated Hugh Hefner for two years. When they broke up, they fought over the custody of the dog they had together. At the time, she was about 25 years old. While living at the Mansion, she met her future husband, Gene Simmons, AKA the Demon from KISS. They remain married to this day.

8 Carrie Leigh

While Shannon Tweed has nothing bad to say about her Bunny years, Carrie Leigh is among the more critical voices. "When you live in an environment like that that's so different from how other people live, you start forgetting who you are and what you believe is right," she told the Washington Post in 1999, likening the house to a cult. She sued Hefner three times and lived with him from 1983 to 1988.

7 Wife #2: Kimberley Conrad

Hugh Hefner didn't stay single for too long. A year later, in 1989, he married Kimberley Conrad and stayed married with her until 2010. However, they had separated years before and lived close by.

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She was 26 when they tied the knot, while he was over 60 years old already. They have two children together, Cooper and Marston Hefner. The divorce wasn't without its problems: she sued him for $4 million.

6 Brande Roderick + others

Hugh Hefner was pushing seventy years old in the nineties, but that didn't discourage him to keep on dating. After he separated with his second wife, he dated several other Bunnies, including Brande Roderick. In 2000, she was named the Playmate of the Year - we're sensing a pattern here - but she left the mansion because she wasn't done with her acting career just yet. That's when they split up. After all, Hefner didn't date outside of his personal Shangri-la.

5 Tina Marie Jordan

Tina Marie Jordan is just one of the several women that Hugh Hefner was dating in the early 2000s. He wasn't a monogamous man and made no attempts to hide it. He dated seven women at the same time! Whoever was the Playmate of the Year was typically considered his #1. The inner workings of such an arrangement remain unknown.

4 Izabella St. James

Izabella St. James moved into the mansion in 2002 when she was 27 years old and stayed there for two years. She was one of the seven already-mentioned women that Hefner dated at the same time. In 2006, she published a revealing expose that painted a grim picture of what went on behind the walls of the Playboy Mansion. Being one of Hef's girlfriends meant she got her own room, a $1000 weekly allowance, and infinite money to spend on plastic surgery.

"The carpet in the upstairs hallway also had not been changed in who knows how long. Everything was just old and stale. Archie the house dog would regularly relieve himself on the hallway curtains, adding the scent of urine to the general scent of decay," she famously wrote.

3 Holly Madison, Bridget Marquardt, and Kendra Wilkinson

Among the many women Hugh Hefner dated in the last decade of his life are also Holly Madison, Bridget Marquardt, and Kendra Wilkinson. They were the stars of The Girls Next Door, a reality show that ran for six seasons. In the show's sixth season, the trio was replaced by two identical twins, Karissa and Kristina Shannon.

2 Karissa and Kristina Shannon

In 2008, Hugh Hefner dated two 20 year-old identical twins, Kristina and Karissa. Eventually, they left the Playboy Mansion and joined the Celebrity Big Brother house. Their lives are rather tragic: they had several botched plastic surgeries and they were both arrested for violence. Today, they are 31 years old.

1 Wife 3: Crystal Harris

In December 2010, Hugh Hefner got engaged to the 24 year-old Crystal Harris who eventually became his last wife. After he died in 2017, she got a $5 million house that he had bought for her, while the rest of his fortune went to his children and charities. She hasn't distanced herself from Hef like some his other ex-girlfriends did.

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