Photo: via Playboy
We don’t ask for a lot in this world, so it goes without saying we’re more than pleased when some of our favorite classic celebrity girls model for Playboy, especially when we never expected it. While Playboy has become more of a place for beautiful, nameless women to find their way onto the computer screen, once upon a time it was where celebrity women shined in their prime, like when Sharon Stone gave us a little more Basic Instinct than we could handle or Farrah Fawcett showed us an angel can be a real demon in the sack.
While Playboy had dismissed nudity over the past year (although it’s back), it seems it’s getting a resurgence, which got us thinking about our favorite celebrity centerfolds across the years. Dating back to before some of us were even old enough to look up boobs on the internet, we have some of those hottest Playboy moments, the issues that made us question ever leaving the house again. From Olivia Munn to Drew Barrymore To Charlize Theron and more, without further adieu, we give you our least expected classic celebrity Playboy moments, spanning more than three decades of hot actresses, sexy models and timeless singers. A-freaking-men.
Classic Celebrity Girls We Never Expected to Model for Playboy
More Playboy where that came from: In Honor Of Playboy Cutting Nudity, We Pay Homage To Their Top 13 Covers Of All Time
Celebrity Women in Playboy
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"Charlize Theron (May 1999)"
Photo: via Playboy
She's no stranger to a sex scene, but this devil's advocate expressed her finer points in May 1999, just before her career really took off. She's still one of our favorites, too.
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"Drew Barrymore (January 1995)"
Photo: via Playboy
The 50 First Dates actress may seem all sweet, but she's also the girl who showed her ta tas on David Letterman's show. The '90s were a wild time, man.
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"Ginger Spice (May 1998)"
Photo: via Playboy
It only takes one part spice to show us her girl power, and Ginger Spice, arguably the fieriest of the Spice Girls, did just that in their prime in 1998.
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"Farrah Fawcett (October 1997)"
Photo: via Playboy
Many a grown man spilt boy milk to this classic angel, and her nude modeling only helped to expedite that. Now those men are likely grandfathers, but that doesn't fade the memory of Farrah Fawcett's 1997 Playboy shoot. This was not her only Playboy moment, but she refused to pose nude in her shoots in the '70s. Damn, we miss her.
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"Kim Basinger (February 1983)"
Photo: via Playboy
While this cover took place when the only boobs we were seeing were our mothers', up close and personal, Kim Basinger did the deed well before her iconic role in the original Batman with Michael Keaton. Boy, if she'd shown it in that movie, our childhood might have been very different.
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"Kim Kardashian (December 2007)"
Photo: via Playboy
Before her butt was breaking intangible things like the internet, Kim K. was already making waves with tangible things like actual, physical magazines, including 2007's final issue of Playboy.
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"Madonna (September 1985)"
Photo: via Playboy
Is it a coincidence that Like a Virgin came out around nine months before Playboy gave birth to Madonna's big debut? Apparently, photographer Martin Schreiber captured her in 1979, before her singing had really gone off, and then published them later in 1985 for Playboy.
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"Naomi Campbell (December 1999)"
Photo: via Playboy
Christmas came a few weeks early while we were partying like it was 1999. That, and we feared Y2K would kill us all, but we hung onto this amazing image of Naomi Campbell to make us feel better. Much better.
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"Olivia Munn (July 2009)"
Photo: via Playboy
We remember getting this issue in the mail and thinking, "Blyme! Who be this gorgeous little trinket?" Alright, we didn't say that, but Olivia Munn did blow us away with her Playboy cover pretty early into her fame. So yeah.
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"Sharon Stone (February 1990)"
Photo: via Playboy
We got a taste of Sharon Stone just before her iconic leg spread in Basic Instinct back in 1990, but it wasn't enough so we had to have her back again in time for the holidays in 1992. That was a very, very merry Christmas, indeed.
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"Uma Thurman (September 1996)"
Photo: via Playboy
Shortly after her Pulp Fiction fame but long before she joined the worst blockbuster of all time, Uma Thurman killed it with her 1996 issue of Playboy. Does anyone know if she'll be nude, should there be a Kill Bill Vol. 3 after all?
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"Vanna White (May 1987)"
Photo: via Playboy
Before she was lighting up letters on Wheel of Fortune, Vanna was lighting up Playboy in the late '80s. Did you know she has a book? It's not quite as sexy as her leaving little to our wild imaginations, but then again we were never big on words when pictures were around, especially this one taken by her ex. At 60, she's still never looked better giving us those letters (they light up now, because she's too old to be flipping those fuckers).
