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
Issue: December 1953
Marilyn Monroe became the first-ever Playboy cover girl for the magazine's inaugural issue.
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Jayne Mansfield
Issue: June 1963
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
Issue: December 1979
Welch's tight red swimsuit might have kept her technically covered up, but was insanely sexy nonetheless.
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Steve Martin
Issue: January 1980
Yes, men can post for Playboy too—as comedian Steve Martin proved in 1980.
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Bo Derek
Issue: March 1980
Bo Derek has always been a perfect 10—so she was a natural fit for Playboy.
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Kim Basinger
Issue: February 1983
Bassinger covered the February 1983 issue with flowing curls and sultry bedroom eyes that epitomized her sex appeal.
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Joan Collins
Issue: December 1983
Joan Collins was full Dynasty glam on her December 1983 Playboy cover.
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Goldie Hawn
Issue: January 1985
Goldie Hawn posing in a giant champagne glass? We'll toast to that any day.
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Madonna
Issue: September 1985
Madonna's Playboy cover line? "Unlike a virgin..." We see what you did there, Hef.
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Brooke Shields
Issue: December 1986
Brooke Shields showed off her babydoll face and perfect pout on the December 1986 cover of Playboy.
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Vanna White
Issue: May 1987
We'd like to buy a WOW for this Vanna White cover.
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Vanity
Issue: April 1988
Prince's protégé covered Playboy in April 1988 and May 1985.
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Cindy Crawford
Issue: July 1988
Cindy Crawford and her iconically sexy mole covered Playboy in July 1988.
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La Toya Jackson
Issue: March 1989
LaToya Jackson was the epitome of rock star glam on her 1989 cover.
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Sharon Stone
Issue: July 1990
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
Issue: December 1990
Sherilyn Fenn's December 1990 cover mixed sexy and classy perfectly.
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Shannen Doherty
Issue: March 1994
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
Issue: May 1994
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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Robin Givens
Issue: September 1994
The Head of the Class actress posed in nothing but a beaded choker in 1994.
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Pamela Anderson
Issue: November 1994
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
Issue: January 1995
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
Issue: December 1995
Farrah Fawcett proved she was most definitely ready for her close up with her December 1995 cover.
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Geri Halliwell
Issue: May 1998
Geri Halliwell was there to help Playboy readers spice up their lives in the May 1998 issue.
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Lisa Rinna
Issue: September 1998
Lisa Rinna made a slouchy sweater sexy as hell in the September 1998 issue.
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Charlize Theron
Issue: May 1999
Even Oscar winners have covered Playboy. Case in point: Charlize Theron's May 1999 cover.
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Naomi Campbell
Issue: December 1999
Naomi Campbell was a barely-wrapped gift to the world on the December 1999 cover of Playboy.
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Kiana Tom
Issue: May 2002
The original fitspo, Kiana Tom, covered Playboy in gold underwear in 2002.
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Kristy Swanson
Issue: November 2002
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
Issue: December 2002
Burlesque queen Dita Von Teese went full pin-up for the December 2002 issue.
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Tia Carrere
Issue: January 2003
Tia Carrere was a sultry, damp-haired goddess on the January 2003 cover.
Kayleigh RobertsKayleigh 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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