The 13 most iconic Playboy covers of all time

As chosen by Playboy.

Lips iconic Playboy covers Loaded
Smoking The Playboy cover has been adorned by some of the biggest names in the world. Image Pictures Playboy

In the biggest nuddy news of 2015 alongside Justin Bieber flashing his arse on a boat, Playboy announced in October that they’re to stop publishing fully naked shoots.

With a history that has taken sex in the States from underground to omnipresent, editor Hugh Hefner has enjoyed a long tenure at the helm, with the magazine’s best-selling issue shifting over seven million copies in November 1972.

But with an immeasurable amount of porn just one click away on the internet nowadays Playboy has lost its controversial edge, and subsequently decided to redefine the brand. The magazine will still reportedly feature women in provocative poses, but no longer fully nude, instead focusing on content a little less NSFW.

As we prepare to kiss goodbye to the Playboy nude shoot, a cornerstone of American culture, we run down the most iconic covers in the magazine’s rich history, as chosen by Playboy.




Marilyn Monroe
December 1953

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The first issue, featuring Marilyn Monroe on the cover, was created by Hugh Hefner on the kitchen table of his South Side Chicago apartment – financed with $600 of Hefner’s money and less than $8,000 of capital.

The magazine appeared on newsstands in December 1953 and the cover was produced undated, just in case there wasn’t a second issue. It sold more than 51,000 copies.


Janet Pilgrim
July 1955

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This wasn’t the first bikini on a Playboy cover, but it was the first time the swimsuit was modeled in such a prominent fashion. (The first bikini cover was July 1954, but the swimsuit was washed ashore, so the cover model wasn’t wearing it).

The model on the beach towel is Janet Pilgrim, who began work at in the magazine’s offices before being asked to appear as the July 1955 issue’s Playmate Of The Month.


Donna Michelle
May 1964

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Hugh Hefner and his artistic staff never lost focus of the two best cover elements: the model and the Rabbit Head logo. On the May 1964 cover Playmate Of The Year Donna Michelle, wearing a white leotard, became the brand.

“I had this idea of a girl posing in the shape of the Rabbit, but I thought no model would be able to do it,” said Art Paul, Playboy’s first art director. “I asked Donna and there was no problem. She got into that position with great ease and could still smile.”

It marked the first time the Playmate Of The Year had been featured so prominently on the cover.


Not Ursula Andress
June 1965

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Some of Playboy’s simplest covers appeared in the 1960s. This cover featured just a redhead in a head-wrap, staring intently above her sunglasses. Cutting off at the nape of her neck, the cover resembles more of a sculptured bust than a traditional men’s magazine cover.

Playboy definitely took a risk with this: As written on the left lens, there’s a 12-page pictorial of Ursula Andress inside. Considering her popularity at the time, it would have been a much safer move to give her the cover.


Barbi Benton
July 1969

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This issue’s cover model was Barbi Benton, Hugh Hefner’s girlfriend for eight years. She would appear on three more covers in the upcoming two decades: March 1970, May 1972 and December 1985. However, she was never named a Playmate Of The Month. So much for favouritism.


Darine Stern
October 1971

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By placing its first African-American model on the cover — the radiant Darine Stern — Playboy was helping shift the standards of mainstream beauty in the nation’s culture. Although the magazine had already featured two black Playmates by this time – March 1965’s Jennifer Jackson and October 1969’s Jean Bell — nude African-American models were mainly seen in publications produced for and by the black communities.

Stern was such a groundbreaking image that it was chosen by the American Society Of Magazine Editors in 2005 as one of the 40 most important magazine covers of the previous 40 years.


Pamela Anderson
October 1989

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Pamela Anderson holds the record for the most Playboy covers — a total of 13. This issue marked her first cover appearance. She has since been featured on the following covers: February 1991; July 1992; August 1993; November 1994; January 1996; September 1997; June 1998; February 1999; July 2001; May 2004; January 2007; and January 2011.

Pammie was also Playboy’s Playmate Of The Month in February 1990. Get collecting the set now, Baywatch fans.


Anna Nicole Smith
June 1993

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Anna Nicole Smith first appeared on Playboy’s March 1992 cover. Within months, she was named Miss May 1992 and Guess jeans’ spokesmodel (yes, that is a word). Smith went on to be named Playboy’s 1993 Playmate Of The Year (featured on this cover), and appeared on three more Playboy covers. In 1994, Smith became infamous for her marriage to 80-something billionaire J Howard Marshall. It was never going to last, and Marshall died the following year. The doomed Smith died of a drug overdose in 2007, a year after her son Daniel died. Makes that Playboy cover a little less enticing, really.


Jenny McCarthy
January 2005

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Jenny McCarthy has appeared on a total of six Playboy covers, including this January 2005 issue where she wore the famous Bunny Costume. She was first named Playboy’s October 1993 Playmate Of The Month and went on to become the magazine’s 1994 Playmate Of The Year.

Her last appearance was in August 2012, since when she has gone on to host successful chat show The View on the ABC network in the US.


Seth Rogen
April 2009

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In Playboy’s 60-year history the magazine has only featured a male on the cover 10 times: Peter Sellers (April 1964); Burt Reynolds (October 1979); Steve Martin (January 1980); Donald Trump (March 1990); Dan Aykroyd (August 1993); Jerry Seinfeld (October 1993); Leslie Nielsen (February 1996); Gene Simmons (March 1999); Seth Rogen (April 2009); and Bruno Mars (April 2012). None of them have been noticeably naked.


November 2013

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Playboy has recently returned to running the more art-inspired, concept covers that the magazine was known for in the 1950s-70s. Photographed by Tony Kelly and art directed by Mac Lewis, this ‘Lips’ cover was recently awarded Cover Of The Day by the Society Of Professional Designers.


Kate Moss
January/February 2014

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Playboy magazine celebrated its 60th anniversary with this issue, which featured a stunning 40-year-old Kate Moss in an unprecedented 18-page pictorial and cover appearance photographed by Mert & Marcus.

Inside Moss was interviewed by Tom Jones, who asked who would be on her ultimate guest-list at a party. “Well, I would like to have dinner with naughty people who have a story to tell — like you!” Moss answered, before listing Jack Nicholson, David Bailey, Stevie Nicks, Catherine Deneuve, Joan Collins, husband Jamie Hince and “obviously” Hugh Hefner. The big creep.


Pamela Anderson (again)
January/February 2016

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Pamela Anderson was featured on the cover and in a 12-page pictorial inside the magazine’s last nude issue. Hugh Hefner said 49-year-old Anderson was the obvious choice for the nude farewell, which was accompanied by an interview with acting eccentric and regular Playboy contributor James Franco.

Anderson’s historic shoot was photographed at the Playboy Mansion by Ellen von Unwerth. Doubtless future non-nude covers will be just as celebrated.

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