Big Tit Celebrities

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

Kim Basinger, Brooke Shields & Goldie Hawn

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.

Heidi Klum

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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.

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Marilyn Monroe

An incredible set of personal items belonging to the late Playboy boss Hugh Hefner is set to hit the auction block, including his original copy of the first ever magazine. The impressive sale is set to take place with Julien's Auctions in LA on November 30 and December 1. The unique auction will give buyers the chance to taste Hefner's lavish life, with intimate items up for auction including his famous silk pyjamas, a smoking jacket, his passport and even his leather bound bible. The main highlight of the sale is an astonishing volume of Hefner's personal Playboy Magazines, which are expected to fetch a whopping $40,000. Included in the volume is Hefner's personal copy of the first ever Playboy Magazine, which features Marilyn Monroe on the front cover. It is expected to sell for $5,000. Another notable item is his Playboy Legacy Collection Gold, a limited edition set of 48 chromogenic and gelatin silver prints by various photographers in a folio wooden case with gold embossed title, published in 2007, which is expected to fetch $30,000. Also up for auction is his personal jukebox, which is expected to sell for $20,000, a personalized Monopoly board, which is expected to make $8,000 and Hefner’s five large folio volumes of Salvador Dali’s 'Biblia Sacra', which is expected to sell for $10,000. 12 Oct 2018 Pictured: Hefner's personal copy of the first issue of Playboy magazine, featuring Marilyn Monroe on the cover. Expected to sell for $5,000. Photo credit: MEGA / Julien's Auctions / MEGA TheMegaAgency.com +1 888 505 6342 (Mega Agency TagID: MEGA291365_001.jpg) [Photo via Mega Agency]

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

American Country and Western Singer Dolly Parton, May 20, 1977 at London?s Hyde Park during her visit to England. (AP Photo/John Glanvill)

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

Kim Basinger during 63rd Annual Academy Awards at Shrine Auditorium in Los Angeles, California March 25, 1991 Credit: Ralph Dominguez/MediaPunch /IPX

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

Goldie Hawn

Goldie Hawn Credit: Ralph Dominguez/MediaPunch /IPX

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

Madonna

Madonna at the 12th Annual American Music Awards January 28, 1985 Credit: Ralph Dominguez/MediaPunch Credit: Ralph Dominguez/MediaPunch /IPX

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 1986 Credit: Ralph Dominguez/MediaPunch /IPX

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

Cindy Crawford

Cindy Crawford at the 1994 MTV Awards. Credit: 3434071Globe Photos/MediaPunch /IPX

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

Pamela Anderson

U.S. actress Pamela Anderson-Lee smiles into the cameras during a press conference in Hamburg, Germany, Feb.6, 1997. Anderson-Lee is staying in Germany to promote a U.S. pizza chain. (AP Photo/Michael Probst)

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 during 1994 MTV Movie Awards at Sony Studios in Culver City, California, United States. (Photo by Jeff Kravitz/FilmMagic, Inc)

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

Drew Barrymore

Actress Drew Barrymore poses backstage at the Hollywood Awards Gala Ceremony, Monday, Oct. 20, 2003, in Beverly Hills, Calif. (AP Photo/Chris Weeks)

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

Jenny McCarthy (Photo by Ron Galella/Ron Galella Collection via Getty Images)

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.

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Lisa Rinna

Actress Lisa Rinna, who was a presenter at the American Music Awards, poses for photographers in Los Angeles, Jan. 27, 1997. (AP Photo/Michael Caulfield)

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

Charlize Theron

South African born actress Charlize Theron poses on the red carpet as she arrives for the U.K. premiere of her new movie 'Hancock', at Leicester Square, London, Wednesday, June 18, 2008. (AP Photo/Simon Dawson)

Charlize Theron went topless for her May 1999 Playboy cover.

Naomi Campbell

British fashion model Naomi Campbell promotes her first perfume at the 'Alsterpalais' in Hamburg (Germany) on 2 September 1999. The fragrance was created by French designer Thierry de Baschmakoff. | usage worldwide Photo by: Kay Nietfeld/picture-alliance/dpa/AP Images

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 during 2005 Fox's 'White Hot Winter' at Meson G Restaurant in Hollywood, California, United States. (Photo by Jon Kopaloff/FilmMagic)

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

Denise Richards

(dpa) - US actress Denise Richards ('007-The World Is Not Enough') arrives for the 'VH1 Big In 2002' Awards in Los Angeles, 4 December 2002. Photo by: Hubert Boesl/picture-alliance/dpa/AP Images

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

Mariah Carey

Singer Mariah Carey arrives at VH1 Save the Music Foundation 10th Anniversary gala in New York, Thursday, Sept. 20, 2007. (AP Photo/Peter Kramer)

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

Kim Kardashian

Socialite Kim Kardashian arrives at the Vegas Magazine's fourth anniversary party held on the closing night of the CineVegas film festival at the Mandalay Bay hotel-casino in Las Vegas on Saturday, June 16, 2007. (AP Photo/Jae C. Hong)

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

Carmen Electra

Actress Carmen Electra poses during the Comic-Con press interview held on Saturday July 26th, 2008 in San Diego, California. (AP Photo/Mark Davis)

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 arrives at the 26th Running of the Breeders' Cup World Championships on Saturday, November 7, 2009 in Santa Anita, CA. (Katy Winn / AP Images for Breeders' Cup)

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

Olivia Munn

Actress Olivia Munn arrives at the Los Angeles Premiere 'The Lovely Bones' at Grauman's Chinese Theatre on December 7, 2009 in Hollywood, California. (Photo by Jon Kopaloff/FilmMagic)

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

Lindsay Lohan

NEW YORK, NEW YORK - NOVEMBER 10: Lindsay Lohan visits 'The Drew Barrymore Show' at CBS Broadcast Center on November 10, 2022 in New York City. (Photo by James Devaney/GC Images)

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

Kate Moss

Moss cameo in Walliams adaptation. File photo dated 13/05/14 of Kate Moss who is to have a cameo role in BBC1's adaptation of David Walliams's children's book The Boy In The Dress. Issue date: Tuesday October 21, 2014. The 40-year-old - who last week appeared in a special edition of Channel 4's Gogglebox, alongside Noel Gallagher and Naomi Campbell - will appear as herself in the film to be shown at Christmas. Moss has previously filmed other guest roles including a brief appearance in a special Sport Relief edition of Absolutely Fabulous in 2012. See PA story SHOWBIZ Moss. Photo credit should read: Chris Jackson/PA Wire URN:21243370

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

Azealia Banks

Singer Azelia Banks arrives at Logo's NewNowNext Awards 2013 at the Fonda Theatre on Saturday, April 13, 2013 in Los Angeles. (Photo by Dan Steinberg/Invision/AP)

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.

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Kylie Jenner

FILE - In this Feb. 9, 2020 file photo, Kylie Jenner arrives at the Vanity Fair Oscar Party in Beverly Hills, Calif. Forbes magazine, which once declared Jenner a billionaire on its cover, says she no longer deserves the title if she ever did, but Jenner is pushing back. Forbes said in a story posted Friday that an examination of financial filings after the reality star and beauty mogul sold 51% of her company Kylie Cosmetics to Coty in a January deal valued at '.2 billion reveal that Jenner’s worth was inflated. (Photo by Evan Agostini/Invision/AP, File)

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