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Hugh Hefner’s life is one of the most enduring legacies of the 20th century. The real-life Great Gatsby truly embodied the American Dream, starting one of the most successful publications in history with just $600 and creating the $110 million dollar Playboy empire.
Striking at exactly the right time, a then 27-year-old Hefner bought nude photographs of Marilyn Monroe, and the rest was history. 
At the time of the first issue’s publication in 1957, Hefner was married to the first woman he slept with, his childhood sweetheart Mildred Williams. However, Hefner and Mildred’s marriage was doomed after she admitted to being unfaithful whilst he was in the military. In an attempt to save the union, Mildred allowed Hefner to sleep with other people, but the two eventually divorced in 1959. 
Now a single man, Hefner went on to live the lifestyle he promoted in his legendary magazine. He broke away from the conservatism that had dominated 1950s American culture, holding lavish parties at his mansion whilst accompanied by hordes of young women. Hefner became so famous for his lifestyle that the world was shocked when he married again in 1989, but, once again, it wasn’t to last, and he separated from his second wife, former Playmate of the Year Kimberly Conrad, in 1998. They finally divorced in 2010. Following the dissolution of his second marriage, Hefner, now a much older man, returned to his old ways, and, at one point, had a staggering seven girlfriends. He eventually downsized to three girlfriends before proposing to a then 24-year-old Playmate Crystal Harris. 
The model, however, got cold feet before their wedding in 2011 and left Hefner, who was 60 years her senior, five days before their wedding. But they reconciled, even though she publically claimed he lasted “two seconds” in bed, and married in December 2012. When Hefner passed away in September of this year, he was worth an estimated $43 million, but now it’s emerged that his beneficiaries, which include his four children from his two marriages, could be unceremoniously cut out his will if they break one simple rule. Despite a shaky start to their marriage, which was viewed with much skepticism after Crystal shamed Hefner on Howard Stern’s radio show, the May-December couple appeared to have a relatively happy union until Hefner’s death this year.
However, Hefner was no fool and prior to marrying Crystal, he made the then 26-year-old sign an “ironclad” prenup. But he wanted her to be “looked after” and left her with $5 million and a luxury home in his will. She along with Hefner’s three children and a small number of other people attended his funeral, which saw him interred in the crypt next to Marilyn Monroe. Check out the video below to see how The King of Playboy himself was laid to rest:
The rest of Hefner’s fortune was left to “his children, the University of Southern California film school, and a variety of charities,” Business Insider reports. He is pictured below with his youngest sons, 26-year-old Cooper and 27-year-old Marston, who he parented with Kimberly Kondrad. Cooper stepped into his late father’s shoes in 2016, taking over as Chief Creative Officer of Playboy Enterprises. 
Hefner’s eldest children from his first marriage, 62-year-old David and 65-year-old Christie, were also listed as beneficiaries in his will. The Playboy founder might have been famed for his life of excess, but over the years, he developed a particular disdain for drugs and alcohol, claiming that they hurt and killed people, and this was something that he did not want his beneficiaries to indulge in. 
So much so that Hefner has specified in his will that if his widow or any of his four children consume or become reliant on drugs that are not prescribed to them, they will lose their right to his fortune. This information was revealed in documents obtained by The Blast. 
The documents also added, “If the Trustees reasonably believe that as a result the beneficiary is unable to care for himself or herself, or is unable to manage his or her financial affairs, all mandatory distributions… to the beneficiary… will be suspended.” If one of Hefner’s beneficiaries suspects another of substance abuse, they have the right to ask for them to take a drug test. However, Hefner is not abandoning them completely, and if they are sober for 12 months, they will have their rights to his fortune restored. Despite serving as Playboy Enterprises Chairman and Chief Executive Officer, Christie rarely gave interviews about her extraordinary father, who is pictured below with his first wife Mildred, however, she recently opened up to People about how his death has affected her.
“We’re fortunate in my family because we really have three families: my brother, David, and me; the two boys, Cooper and Marston, from my dad’s second marriage; and my dad’s wife, Crystal,” she explained. “There’s huge mutual respect and love among all of us, so that’s a kind of funny support system, even though everybody has a different kind of grief.” 
“I feel for the boys because they had their dad for far fewer years than David and I did, and of course Crystal lost a husband,” she said. “It’s not the same, but underlying it all we lost the same person whom we loved. The fact that we’re close and care so much about each other is a huge plus, and it’s something he knew when he was alive.” Christie also made a point of saying that Hefner was “not a person of regrets.” 
“Honestly, even when he sometimes behaved regrettably, he was not good that way,” she said. “Consequently, he wasn’t apt to have a would-have, could-have, should-have attitude about things. How he definitely changed was he found it much easier to express how important people were to him and how much he loved them – not just with family but with other people he was close to.” 
We wish Hugh Hefner’s family and friends our sincere condolences during this difficult time.
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