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59 Celebrities Who Posed for Playboy

From Kim Kardashian and Lindsay Lohan to Heidi Montag.

By Kayleigh Roberts
Magazine, Publication, Album cover, Black hair,
Playboy Magazine

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?

Poster, Album cover, Font, Illustration, Magazine, Art,
Playboy Magazine
1 of 59
Marilyn Monroe

Issue: December 1953

Marilyn Monroe became the first-ever Playboy cover girl for the magazine's inaugural issue.

Illustration, Design, Paper, Advertising, Art,
Playboy Magazine
2 of 59
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.

Magazine, Muscle, Publication, Swimwear,
Playboy Magazine
3 of 59
Raquel Welch

Issue: December 1979

Welch's tight red swimsuit might have kept her technically covered up, but was insanely sexy nonetheless.

Magazine, Album cover, Poster, Publication, Muscle, Advertising, Flesh,
Playboy Magazine
4 of 59
Steve Martin

Issue: January 1980

Yes, men can post for Playboy too—as comedian Steve Martin proved in 1980.

Magazine, Publication, Muscle, Leg, Bikini, Thigh, Sitting, Flesh, Book cover,
Playboy Magazine
5 of 59
Bo Derek

Issue: March 1980

Bo Derek has always been a perfect 10—so she was a natural fit for Playboy.

Hairstyle, Chin, Forehead, Publication, Amber, Magazine, Blond, Poster, Book cover, Eyelash,
Playboy Magazine
6 of 59
Kim Basinger

Issue: February 1983

Bassinger covered the February 1983 issue with flowing curls and sultry bedroom eyes that epitomized her sex appeal.

Magazine,
Playboy Magazine
7 of 59
Joan Collins

Issue: December 1983

Joan Collins was full Dynasty glam on her December 1983 Playboy cover.

Magazine, Album cover, Poster, Flesh,
Playboy Magazine
8 of 59
Goldie Hawn

Issue: January 1985

Goldie Hawn posing in a giant champagne glass? We'll toast to that any day.

Magazine, Poster, Publication, Album cover,
Playboy Magazine
9 of 59
Madonna

Issue: September 1985

Madonna's Playboy cover line? "Unlike a virgin..." We see what you did there, Hef.

Magazine, Lip, Beauty, Album cover, Publication, Book cover, Poster, Photography, Movie, Vampire,
Playboy Magazine
10 of 59
Brooke Shields

Issue: December 1986

Brooke Shields showed off her babydoll face and perfect pout on the December 1986 cover of Playboy.

Magazine, Publication, Book cover, Album cover, Pattern, Brown hair,
Playboy Magazine
11 of 59
Vanna White

Issue: May 1987

We'd like to buy a WOW for this Vanna White cover.

Album cover, Magazine, Poster, Book cover, Flesh, Publication, Fiction, Movie, Fictional character,
Playboy
12 of 59
Vanity

Issue: April 1988

Prince's protégé covered Playboy in April 1988 and May 1985.

Magazine, Hair, Album cover, Beauty, Chin, Publication, Hairstyle, Long hair, Model, Book cover,
Playboy Magazine
13 of 59
Cindy Crawford

Issue: July 1988

Cindy Crawford and her iconically sexy mole covered Playboy in July 1988.

Magazine, Publication, Fetish model, Flesh,
Playboy Magazine
14 of 59
La Toya Jackson

Issue: March 1989

LaToya Jackson was the epitome of rock star glam on her 1989 cover.

Magazine, Hair, Nose, Chin, Blond, Hair coloring, Cheek, Publication, Material property, Brown hair,
Playboy Magazine
15 of 59
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.

Magazine, Publication, Muscle,
Playboy Magazine
16 of 59
Sherilyn Fenn

Issue: December 1990

Sherilyn Fenn's December 1990 cover mixed sexy and classy perfectly.

Magazine, Leg, Publication, Muscle, Flesh, Thigh,
Playboy Magazine
17 of 59
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.

Clothing, Tights, Leg, Pantyhose, Magazine, Thigh, Sitting, Model, Stocking, Human leg,
Playboy Magazine
18 of 59
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.

Magazine, Muscle, Chest, Trunk, Abdomen, Publication, Barechested,
Playboy
19 of 59
Robin Givens

Issue: September 1994

The Head of the Class actress posed in nothing but a beaded choker in 1994.

Magazine, Blond, Album cover, Mouth, Hair coloring, Flesh, Fetish model, Publication,
Playboy Magazine
20 of 59
Pamela Anderson

Issue: November 1994

Pamela Anderson's brand of sex appeal was tailor-made for Playboy, as evidenced by her November 1994 cover.

Magazine, Ear,
Playboy Magazine
21 of 59
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.

Hair, Magazine, Blond, Hair coloring, Hairstyle, Chin, Publication, Material property, Brown hair, Long hair,
Playboy Magazine
22 of 59
Farrah Fawcett

Issue: December 1995

Farrah Fawcett proved she was most definitely ready for her close up with her December 1995 cover.

Magazine,
Playboy Magazine
23 of 59
Geri Halliwell

Issue: May 1998

Geri Halliwell was there to help Playboy readers spice up their lives in the May 1998 issue.

Magazine, Publication, Hair coloring, Book cover, Brown hair,
Playboy Magazine
24 of 59
Lisa Rinna

Issue: September 1998

Lisa Rinna made a slouchy sweater sexy as hell in the September 1998 issue.

Magazine, Skin, Publication, Hair coloring,
Playboy Magazine
25 of 59
Charlize Theron

Issue: May 1999

Even Oscar winners have covered Playboy. Case in point: Charlize Theron's May 1999 cover.

Magazine, Muscle, Leg, Thigh, Publication,
Playboy Magazine
26 of 59
Naomi Campbell

Issue: December 1999

Naomi Campbell was a barely-wrapped gift to the world on the December 1999 cover of Playboy.

Magazine, Publication, Leg, Thigh, Muscle, Flesh,
Playboy
27 of 59
Kiana Tom

Issue: May 2002

The original fitspo, Kiana Tom, covered Playboy in gold underwear in 2002.

Magazine, Flesh, Publication,
Playboy Magazine
28 of 59
Kristy Swanson

Issue: November 2002

The OG Buffy the Vampire Slayer lit the November 2002 cover on fire with a fully-naked pose.

Magazine, Fetish model, Leg, Agent provocateur, Publication, Thigh, Stocking, Black hair,
Playboy Magazine
29 of 59
Dita Von Teese

Issue: December 2002

Burlesque queen Dita Von Teese went full pin-up for the December 2002 issue.

Magazine, Publication, Hair coloring, Book cover, Black hair, Long hair,
Playboy Magazine
30 of 59
Tia Carrere

Issue: January 2003

Tia Carrere was a sultry, damp-haired goddess on the January 2003 cover.

Next
Marilyn Monroe's Life in Photos
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