THE most iconic Playboy covers of all time have been revealed.
Hugh Hefner, founder of the controversial men’s glossy, died last night at the age 91.
Hefner “peacefully passed away today from natural causes at his home, The Playboy Mansion, surrounded by loved ones,” the magazine’s publisher announced.
A host of famous faces have graced the cover of Playboy, including Katie Price, Pamela Anderson and Kate Moss.
Playboy launched in December 1953 with Marilyn Monroe (she didn’t actually pose for the magazine) on the cover.
Only 54,000 copies of the first issues were printed because Hefner didn’t know if it would be successful and if there would be another issue.
Drew Barrymore was just 19 when she posed for Playboy in January 1995.
The Hollywood actress had already lived a rock-star life – battling substance abuse – when she donned a pair of lace pink knickers and a Bunny Girl T-shirt.
It was around this time the former wild child also flashed David Letterman, a US talk show host, on TV.
Anna Nicole Smith first appeared on the Playboy cover in March 1992, and went on to do four more front pages.
The American model’s most memorable shoot saw her posing in diamond necklace and hot pink gloves under the headline, “$450,000,000 Playmate.”
Playboy ran a special collector’s issue in tribute to Anne Nicole Smith following her death in February 2007.
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Blonde bombshell Pamela Anderson has been posing for Playboy for three decades.
She’s also been on more covers for the magazine than any other person.
The 50-year-old actress has posed topless, clad in a string of pearls, and with her Baywatch co-stars in their iconic red swimsuits.
Meanwhile, Madonna was on the verge of a film career in 1985 when some old nude photographs of her were released in the magazine.
The 59-year-old singer refused to apologise and graced the cover of Playboy, under the headline: “Unlike a virgin… for the very first time.”
But it’s not just gorgeous women from across the pond who have graced Playboy.
Katie Price posed topless on the cover in September 2002, under the heading: “London’s legendary bad girl Jordan”.
She posed in a silver corset belt and belly chain that said “Fox”.
Katie hasn’t ever ruled out returning to the publication, telling The Sun in May: “I did the cover shot for American Playboy before, the editorial by the way, not the Playmate. So yes I would do it again.”
Supermodel Naomi Campbell appeared in a 14-page pictorial in the December 1999 issue.
Shot by David LaChapelle in London, Naomi was 29 at the time and one of the world’s top paid models.
She told the magazine: “I work every hard and I’m worth every cent.”
Revealing how she keeps her famous figure in check, Naomi added: “I never diet. I smoke. I drink now and then. I never work out.”
Kate Moss was given the honour of appearing on the magazine’s 60th anniversary issue in 2014.
The 43-year-old Croydon stunner was seen in the iconic Bunny Girl outfit complete with fluffy tail.
“This is a massive global brand,” Playboy’s editorial director Jimmy Jellinek, commented at the time.
"You need a global icon in order to celebrate that - that was the impetus.
“You're talking about the face of Burberry, the biggest supermodel in the world on the cover of Playboy. She's the perfect partner for us to help launch the next 60 years.
“It started with Marilyn Monroe on the cover of Playboy 60 years ago, an icon for her time. Now we've got Kate Moss!"
Even a few men have appeared on Playboy’s cover.
Donald Trump graced the coveted front page in March 1990, dressed in a dinner suit.
Hefner’s son Cooper said in August that he was “personally embarrassed” that they featured the American President so prolifically.
He added: “We don’t respect the guy.”
Seth Rogen also appeared on cover alongside model and TV host Hope Dworaczyk.
In a cheeky shoot reminiscent of Marilyn Monroe, Rogan holds a fan underneath the model's skirt.
In the accompanying interview, Rogen says he is hoping to become a trendsetter for Jewish guys who look like him.
He joked: "Woody Allen created a look for small, nebbishy Jews, and I'm doing the same for chubby Jewish guys. I created a new look for rotund Jews.
"I have seen more guys lately who kind of look like me. It's an easily attainable look."
In March 2016, Hefner announced the magazine would be dropping the famous nude shoots.
The magazine still features pictures of women in "provocative poses" but not full nudity.
The change in attitude has been blamed on the rise of internet pornography with Playboy Enterprises CEO Scott Flanders telling the Times: "You're now one click away from every sex act imaginable for free. And so it's just passé at this juncture."
Hefner is survived by his third wife Crystal Harris, a former Playboy Playmate who was Miss December 2009.
Paying tribute, the firm behind the magazine described Hefner as "the American icon who in 1953 introduced the world to Playboy magazine and built the company into one of the most recognisable American global brands in history."
His son Cooper said "my father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom.
"He defined a lifestyle and ethos that lie at the heart of the Playboy brand," he continued.
Hefner has four children from his two previous marriages.
His daughter Christie who was born in 1952 and son David, born in 1955, were from his frist marriage to Mildred Williams, who he was with from 1949 to 1959.
His younger two sons – Marston, born in 1990, and Cooper, born in 1991 – were from his marriage to Playboy’s “Playmate of the Year”, Kimberly Conrad.
He split with Kimberley in 2010 – the same year he announced his engagement to his current partner.
At the time of his death, Hefner’s net worth was estimated to be around £40million.
His fortune is believed to have totalled some £160million in years gone by, but was hit hard when Playboy’s stock lost 80 per cent of its value.
Kim Kardashian and Paris Hilton have led tributes to the Playboy boss.
And, Hefner’s wife Crystal Harris, 31, "is not named in his will and won’t inherit anything after signing prenup".
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