How Hugh Hefner lived up to his Playboy reputation/2017/Playboy /

How Hugh Hefner lived up to his Playboy reputation/2017/Playboy /



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 aged 85 that he'd 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 later 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.



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.



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.



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.



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.

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.