Playboy magazine is renowned for its glamorous and bold photography featuring some of the biggest names in Hollywood for decades. From Marilyn Monroe’s iconic centerfold in 1953 to today’s stars, the magazine has played a key role in shaping the culture of celebrity nudity.
Mariah Carey
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Singer Mariah Carey looked a million bucks when she donned the front cover of Playboy in March 2007.
Her feature was dubbed the ‘Sexiest Comeback,’ which included Carey participating in the publication’s infamous ‘20 questions.’
Lindsay Lohan
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Lohan launched in 2012 by appearing on the magazine cover in January of that year.
Then-24-year-old Lohan took part in a raunchy Marilyn Monroe-inspired shoot.
Drew Barrymore
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Drew cemented herself in Playboy history by appearing on the cover of the January 1995 edition.
The iconic shoot didn’t go down well with everyone, however. Barrymore’s godfather, Steven Spielberg, responded by sending her a duvet and telling her to “cover up!”
Farrah Fawcett
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OG Charlie’s Angel star, Fawcett, has donned the cover of Playboy three times in her life.
However, it wasn’t until 1995 that she decided to shock everyone by appearing nude.
Madonna
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Never one to shy away from, well, anything, Madge disrobed for the infamous magazine in 1985.
After nude photos from her past surfaced, the singer unapologetically took control of the situation with the iconic shoot.
Daryl Hannah
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Arguably the best PR for the Kill Bill movie franchise was when deadly viper Daryl Hannah appeared on the front cover of Playboy.
Hannah made the world hot under the collar with a steamy 2003 shoot.
Sherilyn Fenn
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When she visited Hugh Hefner, Fenn confirmed herself as a Twin Peaks fan favorite.
Fenn appeared on the front cover of the December 1990 edition, looking every bit the screen siren she is.
Sharon Stone
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An actor’s most important tool is their body, and Stone admitted she bagged her infamous Basic Instinct role via Playboy.
The actress appeared in the mag in 1990 before securing the iconic role of Catherine Tramell.
Denise Richards
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Former Bond Girl Denise Richards famously revealed all (and we do mean all!) in the December 2004 edition.
The actress recently discussed an awkward conversation with her teen daughters about posing for the shoot.
Naomi Campbell
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Infamous celebrity photographer, David LeChapelle, did the honors for Naomi Campbell’s saucy 1999 spread.
The shoot took place in December of that year and featured raunchy scenes like Campbell pouring milk on herself. Ooh-er!
Dita Von Teese
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Burlesque queen Dita Von Teese has dazzled the pages of Playboy several times.
Her most notable appearance, however, was arguably her feature in the December 2002 edition.
Kim Kardashian
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In 2021, TV star Kim Kardashian famously admitted she regretted her 2007 appearance in the magazine.
Despite initially feeling “honored” to appear, Kardashian wishes her younger self hadn’t been “so trusting.”
Pamela Anderson
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Pamela Anderson has donned the pages of Playboy 14 times in her life, 13 of which were on the front cover.
She was infamously the last star to feature in the final nude edition of Playboy in 2016.
Cindy Crawford
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Supermodel Cindy Crawford got us hot and bothered with her 1998 Playboy appearance.
In a recent interview, Crawford stated she had “no regrets” posing for the publication.
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The country music legend famously donned the bunny ears and appeared as a 1978 playmate.
Dolly ‘fessed up that the feature was done as a birthday gift to her hubby.
Kim Basinger
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The publication infamously referred to Bond Girl, Basinger, as a “looker” and a “knockout” when she donned the front cover.
Basinger appeared in the February 1983 edition just as her career was taking off.
Goldie Hawn
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Before Dita Von Teese made a name for herself by frolicking scantily-clad in a giant martini glass, Goldie Hawn did the honors first.
Hawn was interviewed and posed for the January 1985 edition.
Charlize Theron
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Monster actress, Charlize Theron, hit the pages of Playboy in May 1999 with a raunchy semi-nude shoot.
During the shoot, the actress, who remarkably resembled Playmate, er, mate, Pamela Anderson, dazzled us with her beauty and “come to bed” eyes.
Paris Hilton
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In 2013, socialite Paris Hilton infamously slipped into a bunny suit and had an easter egg hunt with Heff for the April edition.
She also appeared on the front cover of the March 2005 edition and was named “sex star of the year.”
Marilyn Monroe
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Monroe famously appeared on the cover of the first-ever edition of Playboy way back in 1953.
Monroe didn’t deliberately pose for the shoot; Hefner paid her $500 for the rights to previous nudes of the star that had been leaked.
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