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How Hugh Hefner lived up to his Playboy reputation 

Playboy founder Hugh Hefner never lacked women in his life, having been married three times and bedded over a thousand, though the media mogul who died at age 91 on Wednesday said he never found his soulmate.

He tearfully noted in a 1992 New York Times interview: ‘I’ve spent so much of my life looking for love in all the wrong places.’

He acknowledged, at age 85, that ‘I never really found my soulmate.’

It was just a few years ago when Hefner bragged that he had slept with ‘over a thousand’ women.

The Playboy founder insisted he has always been faithful during his marriages, but ‘made up for it’ when he was single.

Playboy magazine founder Hugh Hefner passed away on September 27 at the Playboy Mansion. He was 91 years old. He is seen above (left) with Cooper Hefner at the Annual Midsummer Night’s Dream Party at the Playboy Mansion

In 2013, Hefner revealed he's slept with more than 1,000 women, although he doesn't know the exact number

In 2013, Hefner revealed he’s slept with more than 1,000 women, although he doesn’t know the exact number

Asked by Esquire magazine how many women he has slept with, he said: ‘How could I possibly know? Over a thousand, I’m sure.’

‘There were chunks of my life when I was married, and when I was married I never cheated. But I made up for it when I wasn’t married. You have to keep your hand in.’

The media mogul – who was previously married to Mildred Williams from 1949 to 1959 and Kimberley Conrad, the mother of his sons, Marston, 26, and Cooper, 25, from 1989 to 2010 – said in 2013 he was happier than ever with Crystal Harris and felt ‘very fortunate’ to have found love again so late in life.

The two wed on New Year’s Eve in 2012. 

Ladies' man: Hefner opened up about his sex life and revealed he has played around a fair bit

Ladies’ man: Hefner opened up about his sex life and revealed he has played around a fair bit

Always surrounded by ladies: The Playboy supremo is known for his Playboy girls and has previously had a bevvy of girlfriends live with him

Always surrounded by ladies: The Playboy supremo is known for his Playboy girls and has previously had a bevvy of girlfriends live with him

Hugh – who has two other children, Christie and David, from his relationship with Mildred – said: ‘All our friends think it’s made in heaven. It’s only people who don’t know us, who simply see us as stereotypes in terms of age and beauty.

‘I just feel very, very fortunate to have found her at this stage in my life. I saved the best till last.

‘I want the rest of my life to be very much like it is now. I want it to be like this.’

The magazine magnate used to have multiple live-in girlfriends at the Playboy Mansion and his life with Holly Madison, Bridget Marquardt and Kendra Wilkinson was shown in reality TV series The Girls Next Door.

When he was 56 years old, Hefner invited a 19-year-old, Carrie Leigh, to live with him in the Playboy Mansion

When he was 56 years old, Hefner invited a 19-year-old, Carrie Leigh, to live with him in the Playboy Mansion

Leigh, a Playboy Playmate, would stay with Hefner for five tumultuous years, though the relationship dissolved in acrimony

Leigh, a Playboy Playmate, would stay with Hefner for five tumultuous years, though the relationship dissolved in acrimony

In the late 1970s, Hefner was in a serious relationship with Sondra Theodore, a schoolteacher who would go on to become Playmate of the Month in July 1977

In the late 1970s, Hefner was in a serious relationship with Sondra Theodore, a schoolteacher who would go on to become Playmate of the Month in July 1977

Shannon Tweed, who starred in the Canadian TV series Thrill of a Lifetime, used the show as a platform to rocket to stardom, eventually landing in the page of Hefner's magazine

Shannon Tweed, who starred in the Canadian TV series Thrill of a Lifetime, used the show as a platform to rocket to stardom, eventually landing in the page of Hefner’s magazine

Tweed became Miss November 1981, and she would then become Hefner's girlfriend

Tweed became Miss November 1981, and she would then become Hefner’s girlfriend

Unfortunately, Tweed ended the relationship to continue to pursue an acting career, though she and Hefner stayed in touch. During one of Hefner's parties at the Playboy Mansion, she was introduced to Kiss rocker Gene Simmons. They have been a couple since then

Unfortunately, Tweed ended the relationship to continue to pursue an acting career, though she and Hefner stayed in touch. During one of Hefner’s parties at the Playboy Mansion, she was introduced to Kiss rocker Gene Simmons. They have been a couple since then

Hefner is joined by former girlfriend Barbi Benton (left), and then-girlfriend, Holly Madison,  at the Playboy Mansion in Beverly Hills, California in this July 12, 2005 file photo

Hefner is joined by former girlfriend Barbi Benton (left), and then-girlfriend, Holly Madison, at the Playboy Mansion in Beverly Hills, California in this July 12, 2005 file photo

Hefner married third wife Crystal in a romantic ceremony on New Year’s Eve.

And following the nuptials, Crystal Harris revealed the real reason why she tied the knot with ageing Playboy mogul.

During an appearance on the Huffington Post Live, the model, 30, was asked why she decided to marry the then-86-year-old, to which she replied for ‘more security’.

Harris was Hefner’s third wife – a surprisingly low number for Hef given the number of women he has been with.

His views on the institution of marriage were reportedly formed early in his life, when he married his college sweetheart, Mildred Williams, in 1949.

According to The Hollywood Reporter, Hef was heartbroken when he learned that Williams cheated on him while he was enlisted in the military. 

Williams felt so guilty about her infidelity that she allowed her husband to have extramarital relations of his own. 

In 1989, Hefner would marry for the second time. He wed Kimberly Conrad, Miss January 1988

In 1989, Hefner would marry for the second time. He wed Kimberly Conrad, Miss January 1988

They would divorce ten years later, though the marriage did produce two of Hefner’s children, Christie and David Hefner.

In 1988, Hugh asked his daughter, Christie, to take over as CEO of Playboy Enterprises. 

According to Cosmopolitan, Hefner met Williams at the University of Illinois Urbana-Champaign, where he earned a bachelor’s degree in psychology. 

Hefner has never been shy about flaunting his taste for much younger women.

In 1968, when he was 42 years old, he began dating an 18-year-old, Barbara Klein, who was an extra on the Playboy After Dark series. 

When Hefner suggested that Klein change her name, she agreed, becoming Barbi Benton, who went on to star in B-movies like The Third Girl from the Left and Deathstalker. 

Benton would also go on to appear on television shows Hee Haw and Marcus Welby, MD.

Naturally, she also posed for Playboy magazine.

Arguably her most significant contribution to the Hefner legacy was helping him find the Playboy Mansion on a house-hunting trip with her boyfriend.

In the late 1970s, Hefner was in a serious relationship with Sondra Theodore, a schoolteacher who would go on to become Playmate of the Month in July 1977.

In the early 1980s, Hefner would move on, this time to a young Canadian woman who caught his eye on a television show that aired north of the border. 

Hugh Hefner gets close to Playboy Playmate Jenna Bentley

Hugh Hefner gets close to Playboy Playmate Jenna Bentley

Shannon Tweed, who starred in the Canadian TV series Thrill of a Lifetime, used the show as a platform to rocket to stardom, eventually landing in the page of Hefner’s magazine.

Tweed became Miss November 1981, and she would then become Hefner’s girlfriend.

Unfortunately, Tweed ended the relationship to continue to pursue an acting career, though she and Hefner stayed in touch.

During one of Hefner’s parties at the Playboy Mansion, she was introduced to Kiss rocker Gene Simmons. They have been a couple since then.

Hefner wasn’t finished dating young women who weren’t old enough to legally drink.

When he was 56 years old, Hefner invited a 19-year-old, Carrie Leigh, to live with him in the Playboy Mansion.

Leigh, a Playboy Playmate, would stay with Hefner for five tumultuous years, though the relationship dissolved in acrimony.

The bitterness was so acute that Leigh filed a $35million palimony suit against Hef, only to drop the litigation soon afterward.

Leigh was not finished aiming to take a bite out of Hefner’s empire.

In 2008, she founded Nude, a magazine that was created to directly compete with Playboy.            

In 1989, Hefner would marry for the second time. He wed Kimberly Conrad, Miss January 1988.

They were together for nine years and had two children together – Marston and Cooper.

Though they separated, they never legally divorced. For over a decade, they even lived in close proximity to each other.

In 2010, however, their divorce was finalized after Hefner accused Conrad of infidelity. 

Hefner claimed he was faithful during their marriage, but said Conrad cheated on him ‘early in the relationship’. 

However, he didn’t say with whom. 

The aging lothario found the perfect antidote to the stressful divorce proceedings – inviting three then-19-year-olds into his Playboy Mansion. 

Hefner began living with twins Karissa and Kristina Shannon and Crystal Harris. All three are blondes.  

Read more at DailyMail.co.uk


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