Hugh Hefner’s Legacy: Ten Of The Most Iconic Playboy Covers

Posted on September 28 2017 , at 12:19 pm
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  • The 'ladmag' changed the world by breaking the rules.

Pop icon Hugh Hefner passed away earlier today at the age of 91. The journalist, publisher and entertainment mogul changed the world when he started Playboy sixty-four years ago and broke all the rules with his bold content.

Here are just ten of the most iconic Playboy covers.


1. Hi World, Say Hello To Playboy (December 1953)

Playboy Magazine’s very first issue is probably its most iconic. Created by Hugh himself in the kitchen of his apartment in Chicago, the cover features American bombshell, Marilyn Monroe. Monroe’s nudes hit the stands December 1953 and sold more than 51,000 copies.


2. Black In White (December 1999)

Supermodel, Naomi Campbell, graced the cover of Playboy at the peak of her career with a raunchy fourteen page spread.


3. Bunny Kate (January/February 2014)

When the time came to celebrate their 60th anniversary, Playboy magazine chose Kate Moss to be featured on their cover. The 18 page spread was shot by Mert Alas and Marcus Piggott.

4. Robin Gives It All (September 1994)

Mike Tyson’s ex, Robin Givens, who was once known as ‘the most hated woman in America’, left little to the imagination when she bared it all for Playboy magazine.


5. President Playboy (March 1990)

Taken years before Trump even knew he would be running for the position of POTUS, President Donald’s cover with playmate, Brandi Brandt, has definitely become an iconic one.


6. Sellers’ Cover (April 1964)

Apart from being the first man to cover Playboy magazine, Pete Seller’s cover made waves because of its edgy painting like direction. It showed that Playboy could do more than naked women, it can also be futuristic and forward thinking.

7. Darling Darine (October 1971)

African American model, Darine Stern, rocked her Afro on the cover of Playboy magazine on October 1971. Playing her role in changing beauty standards, Stern’s cover made waves at the time for being so avant garde.


8. Catching Them Young

At nineteen, Drew Barrymore shocked the world when she appeared on the cover of Playboy. Her tender age made it a widely discussed matter of morality.


9. Pamela Pamela (October 1989)

The year Taylor Swift was born was iconic for another reason. Pamela, who holds the record for the most Playboy magazine covers,  13 times to be exact, made her debut on the magazine in October 1989.

10. Keeping Up With Kim (December 2007)

Christmas season seems to be an inspired time for Playboy as they landed yet another cover in December 2007. Fresh off her Ray J sex tape scandal, Kim Kardashian appeared on the cover of Playboy and posed nude.

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