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.
The first issue of Playboy released in 1953 featured non other than Hollywood sex symbol Marilyn Monroe.
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.
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, 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 showed some serious skin in “Basic Instinct,” but two years before that movie, the actress posed for Playboy in 1990.
Before becoming an Oscar-winning actress, Charlize Theron graced the cover of Playboy in 1999.
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.
From “House Bunny” to Playboy bunny, funny girl Anna Faris was on the cover of the magazine, but did not go nude.
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!
Hoping for a career comeback, Lindsay Lohan channeled Marilyn Monroe in her Playboy spread in 2012.
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.
Another supermodel that bared all for the magazine was Naomi Campbell, wearing a barely there white bikini for her 1999 cover.
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.
From “Clueless” to Playboy, at the age of 40 Stacey Dash posed for the magazine.
The “Dancing with the Stars” star showed off more than her dance moves when she posed for the cover of Playboy in 2011.
Before her role as Bible-thumping inmate on “Orange is the New Black,” Taryn Manning posed for Playboy.
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.
Olivia Munn, star of “The Newsroom,” went from comic con hottie to sex symbol when she posed for Playboy.
Along with her record five Sports Illustrated Swimsuit Issue covers, Elle Macpherson has also graced the cover of Playboy.