28 Sep The Most Unexpected Celebrities Who Have Posed For Playboy

On the September 28, 2017, it was announced that Playboy founder and all-round media and social icon, Hugh Hefner, had passed away at the age of 91.

Love it or hate it, there’s no denying that Playboy is something of an institution. First published in 1953 featuring a laid bare Marilyn Monroe in its pages, and since then, the magazine has featured a whole host of notable authors, cartoonists, and public figures.

Posing for Playboy became a career goal for many celebrities out there, but deep down we always knew who we could expect show up in the buff. But once in a while, Playboy featured a celebrity that took us all by surprise, as they got their kit off to pose for some saucy photographs. So, without further ado, here are the most unexpected celebrities ever to pose for Hefner’s legendary magazine.

15. Drew Barrymore

Drew Barrymore was just 19 when she first graced the cover of Playboy back in 1995, and was laid completely bare in its pages. By this time, Barrymore had already been a child star, a drug addict, attempted suicide, and checked into rehab. Let’s not also forget that later on this year, she would go on to flash Letterman live on TV. I think it’s safe to say that appearing on Playboy was probably not even in her top ten rock n’ roll experiences.

14. Teri Polo

Teri Polo is best known for her role in Meet The Parents. Back in the naughties, she really made a name for herself when she appeared on the cover of Playboy, just a few years after being ranked #42 on the Maxim Hot 100 Women of 2002 list. Here’s hoping Teri makes a comeback very soon, if this saucy cover is anything to go by.

13. Lindsay Lohan

Many thought Lindsay Lohan’s Playboy shoot would be something of a trainwreck, considering her tumultuous relationship with the world’s press at the time. Thankfully, her Marilyn Monroe inspired shoot was a complete success, and somewhat helped improve her reputation.

12. Uma Thurman

Back in 1996, Playboy made the controversial decision to buy snaps taken of a topless Uma Thurman at the beach and run them on the cover, even reviving the fuzzy Playboy mascot of the ’60s and ’70s to make things just that little bit creepier.

11. Anna Faris

Faris is apparently getting heckled by builders after appearing on the cover of Playboy and NOT posing naked inside. Some have even demanded a refund. She explained: “I was only on the cover of Playboy – with my clothes on – to promote my movie, House Bunny. Then I was in New York and passing this construction site and the workers were all shouting: ‘Hey Anna, you kept your clothes on. We want our money back.’”

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