59 Celebrities Who Posed for Playboy

From Kim Kardashian and Lindsay Lohan to Heidi Montag.

Playboy Magazine
(Image credit: Playboy Magazine)
Kayleigh Roberts
By Kayleigh Roberts
published

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?

1/59
Marilyn Monroe
(Image credit: Playboy Magazine)

Marilyn Monroe

Issue: December 1953

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

2/59
Jayne Mansfield
(Image credit: Playboy Magazine)

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.

3/59
Raquel Welch
(Image credit: Playboy Magazine)

Raquel Welch

Issue: December 1979

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

4/59
Steve Martin
(Image credit: Playboy Magazine)

Steve Martin

Issue: January 1980

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

5/59
Bo Derek
(Image credit: Playboy Magazine)

Bo Derek

Issue: March 1980

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

6/59
Kim Basinger
(Image credit: Playboy Magazine)

Kim Basinger

Issue: February 1983

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

7/59
Joan Collins
(Image credit: Playboy Magazine)

Joan Collins

Issue: December 1983

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

8/59
Goldie Hawn
(Image credit: Playboy Magazine)

Goldie Hawn

Issue: January 1985

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

9/59
Madonna
(Image credit: Playboy Magazine)

Madonna

Issue: September 1985

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

10/59
Brooke Shields
(Image credit: Playboy Magazine)

Brooke Shields

Issue: December 1986

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

11/59
Vanna White
(Image credit: Playboy Magazine)

Vanna White

Issue: May 1987

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

12/59
Vanity
(Image credit: Playboy Magazine)

Vanity

Issue: April 1988

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

13/59
Cindy Crawford
(Image credit: Playboy Magazine)

Cindy Crawford

Issue: July 1988

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

14/59
La Toya Jackson
(Image credit: Playboy Magazine)

La Toya Jackson

Issue: March 1989

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

15/59
Sharon Stone
(Image credit: Playboy Magazine)

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.

16/59
Sherilyn Fenn
(Image credit: Playboy Magazine)

Sherilyn Fenn

Issue: December 1990

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

17/59
Shannen Doherty
(Image credit: Playboy Magazine)

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. 

18/59
Elle Macpherson
(Image credit: Playboy Magazine)

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.

19/59
Robin Givens
(Image credit: Playboy Magazine)

Robin Givens

Issue: September 1994

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

20/59
Pamela Anderson
(Image credit: Playboy Magazine)

Pamela Anderson

Issue: November 1994

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

21/59
Drew Barrymore
(Image credit: Playboy Magazine)

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.

22/59
Farrah Fawcett
(Image credit: Playboy Magazine)

Farrah Fawcett

Issue: December 1995

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

23/59
Geri Halliwell
(Image credit: Playboy Magazine)

Geri Halliwell

Issue: May 1998

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

24/59
Lisa Rinna
(Image credit: Playboy Magazine)

Lisa Rinna

Issue: September 1998

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

25/59
Charlize Theron
(Image credit: Playboy Magazine)

Charlize Theron

Issue: May 1999

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

26/59
Naomi Campbell
(Image credit: Playboy Magazine)

Naomi Campbell

Issue: December 1999

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

27/59
Kiana Tom
(Image credit: Playboy Magazine)

Kiana Tom

Issue: May 2002

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

28/59
Kristy Swanson
(Image credit: Playboy Magazine)

Kristy Swanson

Issue: November 2002

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

29/59
Dita Von Teese
(Image credit: Playboy Magazine)

Dita Von Teese

Issue: December 2002

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

30/59
Tia Carrere
(Image credit: Playboy Magazine)

Tia Carrere

Issue: January 2003

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

31/59
Daryl Hannah
(Image credit: Playboy Magazine)

Daryl Hannah

Issue: November 2003

Splash star was the sexiest of mermaids on her November 2003 cover. 

32/59
Jaime Pressly
(Image credit: Playboy Magazine)

Jaime Pressly

Issue: February 2004

Jaime Pressly's wet silk slip on the February 2004 cover looked painted on—in the sexiest way.

33/59
Rachel Hunter
(Image credit: Playboy Magazine)

Rachel Hunter

Issue: April 2004

Stacy's Mom herself, Rachel Hunter, wore a classic red teddy for her April 2004 cover.

34/59
Charisma Carpenter
(Image credit: Playboy Magazine)

Charisma Carpenter

Issue: June 2004

Buffy and Angel alum Charisma Carpenter was pure sex in her fully nude cover shot. 

35/59
Denise Richards
(Image credit: Playboy Magazine)

Denise Richards

Issue: December 2004

Denise Richards was dripping in diamonds on her December 2004 cover.

36/59
Jenny McCarthy
(Image credit: Playboy Magazine)

Jenny McCarthy

Issue: January 2005

Jenny McCarthy went full bunny for her 2005 cover.

37/59
Teri Polo
(Image credit: Playboy Magazine)

Teri Polo

Issue: February 2005

Teri Polo wore nothing but a sheet accessorized with a single strawberry for her February 2005 cover.

38/59
Paris Hilton
(Image credit: Playboy Magazine)

Paris Hilton

Issue: March 2005

Paris Hilton wore the sexiest fishnets in the photo for her 2005 cover.

39/59
Bai Ling
(Image credit: Playboy Magazine)

Bai Ling

Issue: June 2005

Bai Ling was a sexy bondage lady for her cover shoot in 2005.

40/59
Tricia Helfer
(Image credit: Playboy Magazine)

Tricia Helfer

Issue: February 2007

Battlestar Galactica star Tricia Helfer's sexiness was out of this world on her February 2007 cover. 

41/59
Mariah Carey
(Image credit: Playboy Magazine)

Mariah Carey

Issue: March 2007

Mariah Carey's tan cut-out one-piece was perfection on her March 2007 cover.

42/59
Amanda Beard
(Image credit: Playboy Magazine)

Amanda Beard

Issue: July 2007

The Olympian posed in nothing but bikini bottoms for the July 2007 issue.

43/59
Garcelle Beauvais
(Image credit: Playboy Magazine)

Garcelle Beauvais

Issue: August 2007

Garcelle Beauvais donned a sheer, multi-colored dress that looked like sexy, sexy body paint for her 2007 cover.

44/59
Kim Kardashian
(Image credit: Playboy Magazine)

Kim Kardashian

Issue: December 2007

Kim Kardashian took the world—and the cover of Playboy—by storm in 2007. 

45/59
Anna Faris
(Image credit: Playboy Magazine)

Anna Faris

Issue: September 2008

The House Bunny star covered Playboy in September 2008 in a pink, two-piece ensemble. 

46/59
Carmen Electra
(Image credit: Playboy Magazine)

Carmen Electra

Issue: January 2009

Carmen Electra's bedroom eyes took centerstage in her 2009 cover.

47/59
Aubrey O'Day
(Image credit: Playboy Magazine)

Aubrey O'Day

Issue: March 2009

Aubrey O'Day was all legs on her March 2009 Playboy cover. 

48/59
Olivia Munn
(Image credit: Playboy Magazine)

Olivia Munn

Issue: July/August 2009

Olivia Munn was peak sexy geek in a red bikini on her summer 2009 cover.

49/59
Heidi Montag
(Image credit: Playboy Magazine)

Heidi Montag

Issue: September 2009

Heidi Montag got dirrrrty in a pure white bikini for her Playboy cover. 

50/59
Chelsea Handler
(Image credit: Playboy Magazine)

Chelsea Handler

Issue: December 2009

Funny lady Chelsea Handler's December 2009 cover was definitely no laughing matter. 

51/59
Tara Reid
(Image credit: Playboy Magazine)

Tara Reid

Issue: January/February 2010

Tara Reid took the smoky eye to the next level on her 2010 Playboy cover. 

52/59
Winter Zoli
(Image credit: Playboy Magazine)

Winter Zoli

Issue: March 2011

Winter Zoli wore the sexiest pair of black lace panties for her cover.

53/59
Taryn Manning
(Image credit: Playboy Magazine)

Taryn Manning

Issue: April 2011

Taryn Manning's abs were as intense as her bangs and her black fishnets on her 2011 cover.

54/59
Karina Smirnoff
(Image credit: Playboy Magazine)

Karina Smirnoff

Issue: May 2011

Karina Smirnoff showed off her amazing dancer's bod on the May 2011 cover.

55/59
Lizzy Jagger
(Image credit: Playboy Magazine)

Lizzy Jagger

Issue: June 2011

Mick Jagger's daughter graced the cover of Playboy in 2011. 

56/59
Lindsay Lohan
(Image credit: Playboy Magazine)

Lindsay Lohan

Issue: January/February 2012

Lindsay Lohan let her inner Mean Girl out for her 2012 turn on the cover of Playboy. 

57/59
Kate Moss
(Image credit: Playboy Magazine)

Kate Moss

Issue: February 2014

Kate Moss donned the iconic Playboy bunny suit for the magazine's 60-year anniversary cover in 2014. 

58/59
Azealia Banks
(Image credit: Playboy Magazine)

Azealia Banks

Issue: April 2015

Azealia Banks' colorful cover was as unique as she is.

59/59
Kylie Jenner
(Image credit: Playboy Magazine)

Kylie Jenner

Issue: September 2019

Travis Scott took Kylie Jenner's 2019 Playboy cover. 

Kayleigh Roberts
Kayleigh Roberts
Weekend Editor

Kayleigh Roberts is a freelance writer and editor with more than 10 years of professional experience. Her byline has appeared in Marie Claire, Cosmopolitan, ELLE, Harper’s Bazaar, The Atlantic, Allure, Entertainment Weekly, MTV, Bustle, Refinery29, Girls’ Life Magazine, Just Jared, and Tiger Beat, among other publications. She's a graduate of the Medill School of Journalism at Northwestern University.

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