Marilyn Monroe, Kim Kardashian, and Donald Trump: The most iconic 'Playboy' cover models

Yahoo Lifestyle

As the news hit the world that Playboy founder Hugh Hefner had passed away, people began reminiscing about the 91-year-old’s many Playboy magazine covers.

Originally pinned as a magazine for men, Playboy magazine was kickstarted in 1953 with a photo of Marilyn Monroe on the makeshift cover.

Over the years, Hefner used his beloved “Playmates” as cover models, as well as some of the world’s biggest celebrities, including Kim Kardashian, Charlize Theron, and Madonna.

Top models also graced the cover (Naomi Campbell and Kate Moss, to name a few), as well as unexpected cover models, such as Marge Simpson (yes, the cartoon) and Donald Trump.

Nude or fully clothed, here are the most iconic cover models in the magazine’s 64-year history.

Read more from Yahoo Lifestyle.

Follow us on Instagram, Facebook, and Twitter for nonstop inspiration delivered fresh to your feed, every day.

 

<p>Iconic actress Marilyn Monroe was the perfect cover model to help launch <em>Playboy</em> magazine. Selling for 50 cents, the first issue was produced in Hugh Hefner’s kitchen. Monroe never posed for the magazine. Instead, Hefner used nude photos of her taken from a calendar. (Photo: Playboy) </p>
Marilyn Monroe, 1953

Iconic actress Marilyn Monroe was the perfect cover model to help launch Playboy magazine. Selling for 50 cents, the first issue was produced in Hugh Hefner’s kitchen. Monroe never posed for the magazine. Instead, Hefner used nude photos of her taken from a calendar. (Photo: Playboy)

<p>Yes, the president of the U.S. was once featured on the cover of <em>Playboy</em>. Dressed in a tux sans jacket, Donald Trump posed smugly next to Playmate Brandi Brandt. (Photo: Playboy) </p>
Donald Trump, 1990

Yes, the president of the U.S. was once featured on the cover of Playboy. Dressed in a tux sans jacket, Donald Trump posed smugly next to Playmate Brandi Brandt. (Photo: Playboy)

<p>To promote the first season of “Keeping up with the Kardashians,” middle sibling Kim posed in a revealing red get-up for the December 2007<em> Playboy</em> cover. Behind-the-scenes footage of the shoot can be seen in one of the first “KUWTK” episodes, where Kris Jenner fawns over her nearly naked daughter. (Photo: Playboy) </p>
Kim Kardashian, 2007

To promote the first season of “Keeping up with the Kardashians,” middle sibling Kim posed in a revealing red get-up for the December 2007 Playboy cover. Behind-the-scenes footage of the shoot can be seen in one of the first “KUWTK” episodes, where Kris Jenner fawns over her nearly naked daughter. (Photo: Playboy)

<p>Surprisingly, Kate Moss never appeared on a <em>Playboy</em> cover” — until the 60th anniversary issue, which saw the supermodel don the iconic ears and tail. (Photo: Playboy) </p>
Kate Moss, 2014

Surprisingly, Kate Moss never appeared on a Playboy cover” — until the 60th anniversary issue, which saw the supermodel don the iconic ears and tail. (Photo: Playboy)

<p>Pamela Anderson holds the record for the most <em>Playboy</em> covers — she’s appeared on 13. Anderson’s first cover was in 1989, and her most recent was in 2011. However, it’s this February 1999 pearl necklace cover that became the most memorable. (Photo: Playboy) </p>
Pamela Anderson, 1999

Pamela Anderson holds the record for the most Playboy covers — she’s appeared on 13. Anderson’s first cover was in 1989, and her most recent was in 2011. However, it’s this February 1999 pearl necklace cover that became the most memorable. (Photo: Playboy)

<p>Before she was a bonafide Hollywood star, Drew Barrymore was a bit of a wild child in the industry. At age 19, she posed in a white <em>Playboy</em> T-shirt and a pair of pink knickers for the 1995 cover. For her 20th birthday, Barrymore’s godfather, Steven Spielberg, sent her a note that said, “Cover yourself up,” with photos of the <em>Playboy</em> shoot edited so that she appeared fully clothed.<br>(Photo: Playboy) </p>
Drew Barrymore, 1995

Before she was a bonafide Hollywood star, Drew Barrymore was a bit of a wild child in the industry. At age 19, she posed in a white Playboy T-shirt and a pair of pink knickers for the 1995 cover. For her 20th birthday, Barrymore’s godfather, Steven Spielberg, sent her a note that said, “Cover yourself up,” with photos of the Playboy shoot edited so that she appeared fully clothed.
(Photo: Playboy)

<p>To celebrate the 20th anniversary of “The Simpsons,” Hugh Hefner went where no other men’s magazine had gone before. He ditched the usual scantily clad models for animated matriarch Marge Simpson, who posed “naked” on a Playboy chair. (Photo: Playboy) </p>
Marge Simpson, 2008

To celebrate the 20th anniversary of “The Simpsons,” Hugh Hefner went where no other men’s magazine had gone before. He ditched the usual scantily clad models for animated matriarch Marge Simpson, who posed “naked” on a Playboy chair. (Photo: Playboy)

<p>Charlize wasn’t happy with her cover, which featured a nude photo taken years earlier. She tried to sue <em>Playboy</em> but was unsuccessful, leaving the somewhat natural-looking shot to be ogled by men across the world. (Photo: Playboy) </p>
Charlize Theron, 1999

Charlize wasn’t happy with her cover, which featured a nude photo taken years earlier. She tried to sue Playboy but was unsuccessful, leaving the somewhat natural-looking shot to be ogled by men across the world. (Photo: Playboy)

<p>Say what you will about <em>Playboy</em>, but the magazine did help to push the industry forward. Darine Stern became the first woman of color to be featured on the magazine’s cover, and this happened in 1971.<br>(Photo: Playboy) </p>
Darine Stern, 1971

Say what you will about Playboy, but the magazine did help to push the industry forward. Darine Stern became the first woman of color to be featured on the magazine’s cover, and this happened in 1971.
(Photo: Playboy)

<p>Madonna is one of the only stars to appear fully clothed on the <em>Playboy</em> cover. However, the inside shoot featured nude photos taken of her in 1978, when she was a struggling singer. (Photo: Playboy) </p>
Madonna, 1985

Madonna is one of the only stars to appear fully clothed on the Playboy cover. However, the inside shoot featured nude photos taken of her in 1978, when she was a struggling singer. (Photo: Playboy)

<p>The British supermodel stripped down for the 1999 Christmas <em>Playboy</em> issue. Posing in a controversial white fur coat, Campbell ended up in a 14-page nude spread in the mag. (Photo: Playboy) </p>
Naomi Campbell, 1999

The British supermodel stripped down for the 1999 Christmas Playboy issue. Posing in a controversial white fur coat, Campbell ended up in a 14-page nude spread in the mag. (Photo: Playboy)

<p>“Dynasty” star Joan Collins was another star who appeared fully clothed in the ’80s. Wearing a glamorous (but admittedly skimpy) red gown, she was the ideal person to front the 1983 Christmas issue. (Photo: Playboy) </p>
Joan Collins, 1983

“Dynasty” star Joan Collins was another star who appeared fully clothed in the ’80s. Wearing a glamorous (but admittedly skimpy) red gown, she was the ideal person to front the 1983 Christmas issue. (Photo: Playboy)

<p>Elle Macpherson showed off her super-long legs on the May 1994 cover. Wearing nothing but a pair of sheer black tights, the Aussie supermodel looked like a modern Brigitte Bardot.<br>(Photo: Playboy) </p>
Elle Macpherson, 1994

Elle Macpherson showed off her super-long legs on the May 1994 cover. Wearing nothing but a pair of sheer black tights, the Aussie supermodel looked like a modern Brigitte Bardot.
(Photo: Playboy)

<p>Dolly Parton is almost unrecognizable on the October 1978 <em>Playboy</em> cover, posing in the iconic Playboy costume to promote her 20th album. (Photo: Playboy) </p>
Dolly Parton, 1978

Dolly Parton is almost unrecognizable on the October 1978 Playboy cover, posing in the iconic Playboy costume to promote her 20th album. (Photo: Playboy)

<p>Back when Katie Price was known as Jordan, the model and her ample assets appeared on the cover under the headline “London’s legendary bad girl.”(Photo: Playboy) </p>
Katie Price, 2002

Back when Katie Price was known as Jordan, the model and her ample assets appeared on the cover under the headline “London’s legendary bad girl.”(Photo: Playboy)

What to Read Next