38 Celebrity Women Who've Been in Playboy: From Marilyn Monroe to Kate Moss & More (2024)

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Julia Teti, Giovana Gelhoren, Delilah Gray

November 15, 2023 at 6:00pm EST

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.
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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 Kardashian made 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.
Jayne Mansfield
Along with being Miss February 1955, Jayne Mansfield was on the peekaboo June 1963 cover.
Sharon Stone
Back in July 1990, Sharon Stone wore only a chunky bracelet for her covershoot.
Shannen Doherty
Shannen Doherty donned only a silk lacey white pj set, along with the doves on her knees for her angelic March 1994 cover.
Vanna White
Vanna White posed in an oversized black and white sweater for the May 1987 cover.
Raquel Welch
Raquel Welch wowed fans with a tight red swimsuit photo for the Dec 1979 cover.
Joan Collins
Joan Collins was the definition of glamorous in a high-slit, Christmas-themed gown for the Dec 1983 shoot.
Farrah Fawcett
The legendary Farrah Fawcett’s Dec 1995 cover shoot was a seductive close-up.
Kristy Swanson
Kristy Swanson wowed in her fully nude cover back in Nov 2002.
Charisma Carpenter
Everyone was obsessed with Charisma Carpenter’s fully nude cover shot back in June 2004.
Daryl Hannah
Daryl Hannah posed fully nude for the Nov 2003 cover.
Dita Von Teese
Dita Von Teese kept all the pin-up vibes for her topless cover for Dec 2002.
Heidi Montag
Back in Sept 2009, Heidi Montag turned up the heat with her white bikini photoshoot.
Anna Faris
Anna Faris unleashed her House Bunny character for the Sept 2008 cover.