When Hugh Hefner’s first marriage to his childhood sweetheart Mildred Williams ended in divorce in 1959, he began to live the Playboy lifestyle that we have all come to associate with the world’s most famous bachelor.

Against the odds he decided to tie the knot again in 1989, marrying Playmate of the Year Kimberly Conrad, only to separate in 1998 after having two children together. Following their divorce, Hefner said that he preferred to be single.

Then in his seventies, he continued to date women a fraction of his age including Holly Madison, Kendra Wilkinson and Bridget Marquardt, pictured below, whose relationships with him were famously depicted on The Girls Next Door.

Although Hefner had three live in girlfriends, Madison was his “number one girlfriend”, and the two shared a more serious relationship. Despite their 53-year age gap, she wanted to marry the Playboy mogul and have his children.

However, Hefner was unwilling to marry again, and when doctors confirmed that his sperm was no longer viable, Madison left him after seven years together. This came shortly after Wilkinson and Marquardt also decided to end their relationships with the man who made them household names.

The trio were almost immediately replaced by then 19-year-old twin playmates Kristina and Karissa Shannon and 23-year-old Crystal Harris, with Harris taking Madison’s place as Hefner’s number one girlfriend.

Harris went on to become a Playmate, posing for the December 2009 issue of Playboy.

Just two years into his relationship with Crystal, Hefner did the unthinkable and proposed. This came as a surprise to Crystal who claimed that she was not looking to marry the Playboy founder, but she accepted the proposal anyway.

But Hefner’s wife-to-be got cold feet five days before their wedding in 2011 and left Hefner during one of his movie nights. She then gave a shocking interview to Howard Stern, claiming that the two only ever slept together once.

“I have never seen him naked… I am not turned on by Hef. Sorry,” she revealed to Stern.

Harris publicly apologized for her comments and ended up marrying Hefner in December 2012, despite friends warning the Playboy founder not to. But, Hefner, clearly a clever man, made sure that he wasn’t going to be taken for a ride…

Hefner and Harris’ 60-year age gap caused many to believe that she was nothing more than a gold digger. This was feeling was intensified after her interview with Stern, which only served to confirm suspicions that their relationship was not genuine.

However, as the founder of one of America’s most successful publications, Hefner ensured that an ironclad prenup was in place before the two tied the knot, and in another bitter twist, Harris was not added to the multi-millionaire’s will.

Hefner’s $43 million fortune will be divided between his four children, the University of Southern California and a list of  charities. The Playboy Mansion was sold in 2016 for $100 million. It is not known what will happen to that money.

At one point, Hefner was worth $200 million, but lost a sizeable portion of his fortune when the popularity of Playboy declined – a change which can undoubtedly be attributed to the availability of pornography on the Internet.

When asked why she finally decided to marry Hefner, Harris said, “Well for me it meant more security, knowing that I am the one for him. There are always girls in and out and always the feeling of maybe being replaced… And he made sure I didn’t feel that way anymore and that was what the wedding was all about.”

Mr and Mrs Hefner went on to share a seemingly happy four and half year marriage before Hefner’s death on September 27.

“I made the commitment, quite frankly, because I felt that I had, in a previous relationship with Holly, not been there for her in a way that she wanted me to be,” Hefner said.

“All our friends think it’s made in heaven,” Hefner added. “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.”

Madison was positive about her relationship with Hefner until 2015 when she released an explosive tell-all, Down the Rabbit Hole, which portrayed Hefner has a manipulator who pitted his girlfriends against each other for his own gain.

She has yet to publicly comment about her former partner’s death.