25 Celebrity Women Who’ve Been in Playboy: From Marilyn Monroe to Kate Moss & More

Since its inception in the mid 1950s, Playboy magazine has courted fascination as well as controversy. Whether the magazine’s founder, Hugh Hefner, was positioning the outlet as a pioneer of the sexual revolution, or if history and investigative pieces uncovered the misogyny that was happening behind the scenes, Playboy has been a longstanding cultural pillar for decades. The outlet has ushered in a new era within the past few years, and even in the years prior to Hefner’s death in 2017, the magazine has catered to thought-provoking essays.

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But Playboy’s roots are deeply embedded in the covers that made the outlet such a lightning rod for controversy and conversation. Dating all the way back to its first issues in the ‘50s, a number of famous women have appeared on the cover and in the photo spreads of Playboy. Of course, it’s no surprise that one of the very first women to make an appearance on the cover was Marilyn Monroe.

The stunning blonde beauty was, and largely remains, the epitome of sex appeal. As time went on, Playboy featured even more stars like actress Drew Barrymore, models Brooke Shields and Naomi Campbell, comedian Chelsea Handler, and one of Kim Kardashian’s first major covers was with Playboy, too.

There have been so many famous faces on the cover of this magazine, and some of them might surprise you. Take a look at our roundup of 25 famous women who posed for Playboy.

Marilyn Monroe

Playboy’s first issue came out in December 1953. One of the first women to grace the cover was none other than Marilyn Monroe, photographed here for the magazine.

Dolly Parton

Decades later, country singer Dolly Parton made her Playboy debut in 1978. Another couple of decades went by before Parton actually donned her bunny ears again and recreated her cover just for her husband’s birthday.

Kim Basinger

At the height of her career in the ’80s, Kim Basinger posed for Playboy for the magazine’s February 1983 issue.

Goldie Hawn

For the January 1985 issue, Goldie Hawn posed in a giant martini glass on the cover of Playboy.

Madonna

Madonna looked like an absolute pop diva on her September 1985 cover, decked out in high-waisted trousers, a lace and sheer corset top, and blazer.

Brooke Shields

Brooke Shields‘ December 1986 Playboy cover featured the longtime model wearing giant red ornaments as earrings.

Cindy Crawford

In July 1988, Cindy Crawford stripped down for her Playboy photo shoot.

Pamela Anderson

Pamela Anderson‘s edgy sex appeal was the perfect fit for Playboy. She appeared on a number of the magazine’s covers.

Elle MacPherson

Elle MacPherson looked sexy only wearing black tights for Playboy’s May 1994 issue.

Drew Barrymore

Drew Barrymore‘s January 1995 Playboy cover featured the actress wearing a white T-shirt with the iconic Playboy bunny symbol embossed on the fabric.

Jenny McCarthy

Known as one of the Playboy playmates that most achieved success, Jenny McCarthy graced the cover of the magazine many times. Issues of her include June 1994, July 1996, December 1996, September 1997, January 2005 and July 2012.

Lisa Rinna

Lisa Rinna look so sexy in Playboy’s September 1998 issue.

Charlize Theron

Charlize Theron went topless for her May 1999 Playboy cover.

Naomi Campbell

For the December 1999 issue, Naomi Campbell wore a barely-there bra and underwear set with a luxurious white fur wrap.

Paris Hilton

Paris Hilton looked fun and flirty in a red corset and black fishnet tights for the March 2005 issue of Playboy.

Denise Richards

Denise Richards also got the holiday treatment for her Playboy cover, appearing in the magazine’s December 2004 issue.

Mariah Carey

Mariah Carey sported a cut-out one-piece on the cover of the March 2007 issue of Playboy.

Kim Kardashian

Burgeoning reality TV star Kim Kardashianmade her Playboy debut for the December 2007 issue of the magazine.

Carmen Electra

Playboy kicked off 2009 with Carmen Electra as their cover star, posing for the January 2009 issue and so many more.

Chelsea Handler

Chelsea Handler brought her signature wit to her December 2009 Playboy cover.

Olivia Munn

Olivia Munn looked like a bond girl emerging from the water in the magazine’s July/August issue back in 2009.

Lindsay Lohan

Lindsay Lohan looked gorgeous in the Marilyn Monroe-inspired cover for Playboy’s January/February 2012 issue.

Kate Moss

For the magazine 60th anniversary, Kate Moss wore the iconic bunnysuit, including ears, for Playboy’s February 2014 issue.

Azealia Banks

Azealia Banks made her Playboy debut in September 2017. “It was an absolute honor to be chosen as the first female rapper to make the cover of playboy magazine. May your legacy live on,” she wrote as her caption upon posting the cover to Instagram.

Kylie Jenner

In September 2019, Kylie Jenner followed in big sis Kim Kardashian’s foot steps and pose for her own Playboy cover.