The colourful life and many loves of Playboy founder Hugh Hefner

Hugh Hefner has died age 91, and after his long and colourful life the Playboy founder will always be remembered as someone far from ordinary.

The first issue of his signature publication, Playboy magazine, gained notoriety after it featured a nude photograph of Marilyn Monroe in 1953.

In that same year the then-27-year-old established his own lifestyle and media company Playboy Enterprises, Inc. He served on company's board right up until his death.

By the 60s, the brand's logo had become iconic.

"The rabbit, the bunny, in America has a sexual meaning; and I chose it because it’s a fresh animal, shy, vivacious, jumping — sexy" Hugh told People in 1967.

Of course his unconventional love life wasn't always so unconventional, with Hugh marrying first wife Mildred Williams in 1949, with the couple welcoming children Christie and David during their decade-long union.

However following their divorce the notorious womanizer was open about his many lovers and the many women he shared his life with.

In 1989 Hugh married Playmate of the Year Kimberley Conrad, and went on to have two more children the model- sons Marston Glenn and Cooper Bradford- however his second marriage would end a decade later, with the pair officially divorcing in 2010.

In 2001, Hugh infamously had mulitple girlfriends, with former number one girlfriend Holly Madison writing in her autobiography Down The Rabbit Hole, listing them as Cathi O'Malley, Buffy Tyler, Tina Jordan, Tiffany Holliday, Stephanie Heinrich, Kimberley Stanfield, and Regina Lauren, with other outlets adding Katie Lohmann and Izabella St. James were also on Hugh's "girlfriend roster".

Shortly afterwards Hugh cuts his girlfriend list down, with Holly, Bridget Marquardt and Kendra Wilkinson becoming his main girlfriends until 2008, and even getting their own reality show The Girls Next Door.

The reality show, which ran over six seasons, documented the three women's live inside the famous Playboy Mansion, which Hugh bought in 1971, and their relationship with the magazine mogul.

After the demise of his relationships to Holly, Bridget and Kendra, Hugh became involved with twins Kristina and Karissa Shannon and future wife Crystal Harris.

At age 86, Hugh married 26-year-old Crystal in December 2012 after the model called off their previous wedding plans in June 2011.

In August 2016, Hugh sold the Playboy Mansion for $200 million to Daren Metropoulos, who already lived next door to the famous property, however there was a special clause in the final deal that meant he was able to live there until his death.

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The mansion was well-known for its parties, with the Halloween party one of the biggest annual events.

Only last month Hugh's son Cooper, who took over from his father as CEO of Playboy, said it was hard to watch his dad "struggle" as he got older.

"It’s tough to watch him struggle. But I’m just happy it’s physical and not mental," Cooper told The Hollywood Reporter.

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