20 Stylish Celebrities You Didn’t Know Posed In Playboy

Hugh Hefner must be one convincing man. Some of the most stylish celebrities have traded their designer threads for their birthday suit for Hefner's Playboy magazine. From Marilyn Monroe to Madonna to Naomi Campbell, some of the world's most stylish singers, actresses and models have bared all for the magazine. Before winning her Oscar, Charlize Theron posed nude for Playboy. At the age of 40, Kate Moss graced the cover for the magazine's 60th anniversary. And hoping for a career comeback, Lindsay Lohan embodied Marilyn Monroe for her Playboy spread. These red carpet darlings, and many more, all have their Playboy bunny ears. Check out our gallery below to see more stylish stars you didn't know posed for Playboy. Marilyn Monroe
Photo: WENN
Marilyn Monroe The first issue of Playboy released in 1953 featured non other than Hollywood sex symbol Marilyn Monroe.
Estee Lauder Modern Muse
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Drew Barrymore We all know Drew Barrymore as the quirky actress, but at age 19 Barrymore was on the cover of the magazine. Now, 20 years later she reveals she wouldn't want her daughter posing for Playboy.
The 2013 British Fashion Awards
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Kate Moss Sure, Kate Moss has been on the covers of fashion magazines from Vogue to Elle, but who knew the supermodel is also a Playboy bunny? Moss posed for the magazine's 60th anniversary in 2014.
Marge Simpson
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Marge Simpson Marge Simpson, the most stylish animated housewife, became the first cartoon on the Playboy cover when she emulated past bunny Darine Stern's iconic 1971 cover.
Sharon Stone PF WENN
Photo: WENN
Sharon Stone Sharon Stone showed some serious skin in "Basic Instinct," but two years before that movie, the actress posed for Playboy in 1990.
Variety's 5th Annual Power Of Women Event
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Charlize Theron Before becoming an Oscar-winning actress, Charlize Theron graced the cover of Playboy in 1999.
Sean Penn 3rd Annual Help Haiti Home Gala Benefiting J/P HRO Presented By Giorgio Armani
Photo: WENN
Chelsea Handler Comedienne Chelsea Handler has no shame when it comes to her sex life, so it shouldn't come as a surprise that she rocked some knee-high boots and a barely there bikini for her Playboy cover.
CW, CBS and Showtime 2013 Summer TCA Party
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Anna Faris From "House Bunny" to Playboy bunny, funny girl Anna Faris was on the cover of the magazine, but did not go nude.
Entertainment Weekly Screen Actors Guild Party
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Lisa Rinna It takes a lot of courage to pose for Playboy, and Lisa Rinna not only graced the cover but did it while she was pregnant!
Z100 jingle ball at MSG
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Lindsay Lohan Hoping for a career comeback, Lindsay Lohan channeled Marilyn Monroe in her Playboy spread in 2012.
Photo: WENN
Madonna Before Madonna became the superstar she is today, old nude photos of the singer surfaced. Instead of apologizing, Madonna posed for the cover of the magazine.
Oxygen Celebrates the Premiere of "THE FACE" at The Marquee nightclub
Photo: WENN
Naomi Campbell Another supermodel that bared all for the magazine was Naomi Campbell, wearing a barely there white bikini for her 1999 cover.
Vanna White
Photo: WENN
Vanna White Although she never posed for the magazine, photos taken by a boyfriend of the "Wheel of Fortune" letter turner Vanna White were published in the magazine.
Stacey Dash
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Stacey Dash From "Clueless" to Playboy, at the age of 40 Stacey Dash posed for the magazine.
29th Santa Barbara International Film Festival - Virtuosos Award Ceremony
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Karina Smirnoff The "Dancing with the Stars" star showed off more than her dance moves when she posed for the cover of Playboy in 2011.
Photo: WENN
Taryn Manning Before her role as Bible-thumping inmate on "Orange is the New Black," Taryn Manning posed for Playboy.
Cindy Crawford
Photo: WENN
Cindy Crawford Cindy Crawford has posed for Playboy not once, but twice. The supermodel first graced the cover in 1988, and ten years later she did it again. Of the experience Crawford said, "As long as I could do it with Herb, it was a no brainer," referring to famed photographer Herb Ritts.
BVLGARI Presents "Decades Of Glamour"
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Olivia Munn Olivia Munn, star of "The Newsroom," went from comic con hottie to sex symbol when she posed for Playboy.
Elle MacPherson
Photo: WENN
Elle Macpherson Along with her record five Sports Illustrated Swimsuit Issue covers, Elle Macpherson has also graced the cover of Playboy.
Tom Ford Cocktail Party
Photo: WENN
Garcelle Beauvais "The Jamie Foxx Show" star Garcelle Beauvais posed for Playboy at the age of 40, and looked fantastic.

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  • Nessa Fox

    time to hit google..

  • GrumpyCat

    Okay, either I am really in the know or that was the worst “You didn’t know” list ever. I think only 2 actresses I didn’t know posed for playboy.