For many icons, from Madonna to Naomi Campbell, a Playboy cover is a rite of passage. The photos are visceral, tantalizing, and for many celebrities, incredibly empowering. Marilyn Monroe kicked off the trend in 1953 as the first-ever Playboy cover star, and dozens of icons since have adorned the cover of the magazine, now a byword for unapologetic sexiness. If you forgot about the icon covers from Kim Kardashian, Anna Faris, Brooke Shields, and more, well—we’re here to remind you. Let’s take a trip down memory lane, shall we?
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Marilyn Monroe
Marilyn Monroe became the first-ever Playboy cover girl for the magazine’s inaugural issue.
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Jayne Mansfield
Mansfield’s peek-a-boo cover is iconic—and not even her first appearance in the magazine. She was also Miss February 1955.
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Raquel Welch
Welch’s tight red swimsuit might have kept her technically covered up, but was insanely sexy nonetheless.
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Steve Martin
Yes, men can post for Playboy too—as comedian Steve Martin proved in 1980.
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Bo Derek
Bo Derek has always been a perfect 10—so she was a natural fit for Playboy.
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Kim Basinger
Bassinger covered the February 1983 issue with flowing curls and sultry bedroom eyes that epitomized her sex appeal.
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Joan Collins
Joan Collins was full Dynasty glam on her December 1983 Playboy cover.
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Goldie Hawn
Goldie Hawn posing in a giant champagne glass? We’ll toast to that any day.
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Madonna
Madonna’s Playboy cover line? “Unlike a virgin…” We see what you did there, Hef.
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Brooke Shields
Brooke Shields showed off her babydoll face and perfect pout on the December 1986 cover of Playboy.
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Vanna White
We’d like to buy a WOW for this Vanna White cover.
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Cindy Crawford
Cindy Crawford and her iconically sexy mole covered Playboy in July 1988.
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La Toya Jackson
LaToya Jackson was the epitome of rock star glam on her 1989 cover.
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Sharon Stone
Sharon Stone will do down in history as one of the biggest sex symbols in Hollywood history. Her 1990 Playboy cover illustrates why.
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Sherilyn Fenn
Sherilyn Fenn’s December 1990 cover mixed sexy and classy perfectly.
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Shannen Doherty
Shannen Doherty has never done anything that wasn’t unique and her doves-on-knees Playboy cover was no different.
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Elle Macpherson
Elle Macpherson covered the May 1994 issue in nothing but a pair of black pantyhose. The cover, naturally, went down in Playboy history.
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Pamela Anderson
Pamela Anderson’s brand of sex appeal was tailor-made for Playboy, as evidenced by her November 1994 cover.
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Drew Barrymore
Drew Barrymore went meta for her cover shoot, donning a Playboy bunny shirt, a coy smile, and a lacy pair of pink panties.
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Farrah Fawcett
Farrah Fawcett proved she was most definitely ready for her close up with her December 1995 cover.
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Geri Halliwell
Geri Halliwell was there to help Playboy readers spice up their lives in the May 1998 issue.
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Lisa Rinna
Lisa Rinna made a slouchy sweater sexy as hell in the September 1998 issue.
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Charlize Theron
Even Oscar winners have covered Playboy. Case in point: Charlize Theron’s May 1999 cover.
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Naomi Campbell
Naomi Campbell was a barely-wrapped gift to the world on the December 1999 cover of Playboy.
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Kristy Swanson
The OG Buffy the Vampire Slayer lit the November 2002 cover on fire with a fully-naked pose.
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Dita Von Teese
Burlesque queen Dita Von Teese went full pin-up for the December 2002 issue.
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Tia Carrere
Tia Carrere was a sultry, damp-haired goddess on the January 2003 cover.
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Daryl Hannah
Splash star was the sexiest of mermaids on her November 2003 cover.
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Jaime Pressly
Jaime Pressly’s wet silk slip on the February 2004 cover looked painted on—in the sexiest way.
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Rachel Hunter
Stacy’s Mom herself, Rachel Hunter, wore a classic red teddy for her April 2004 cover.
Kayleigh Roberts
Kayleigh Roberts is the weekend editor at Marie Claire, covering celebrity and entertainment news, from actual royals like Kate Middleton and Meghan Markle to Hollywood royalty, like Katie Holmes and Chrissy Teigen.
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