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.