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.