59 Celebrities Who Posed for Playboy

(Image credit: Playboy Magazine)

By Kayleigh Roberts 2019-10-12T08:57:01Z

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

Issue: December 1953

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

2/59

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.

3/59

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

Issue: January 1980

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

5/59

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

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

Issue: December 1983

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

8/59

Goldie Hawn

Issue: January 1985

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

9/59

Madonna

Issue: September 1985

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

10/59

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

Issue: May 1987

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

12/59

Vanity

Issue: April 1988

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

13/59

Cindy Crawford

Issue: July 1988

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

14/59

La Toya Jackson

Issue: March 1989

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

15/59

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.

16/59

Sherilyn Fenn

Issue: December 1990

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

17/59

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.

18/59

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.

19/59

Robin Givens

Issue: September 1994

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

20/59

Pamela Anderson

Issue: November 1994

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

21/59

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.

22/59

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

Issue: May 1998

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

24/59

Lisa Rinna

Issue: September 1998

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

25/59

Charlize Theron

Issue: May 1999

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

26/59

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

Issue: May 2002

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

28/59

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

Issue: December 2002

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

30/59

Tia Carrere

Issue: January 2003

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

31/59

Daryl Hannah

Issue: November 2003

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

32/59

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

Issue: April 2004

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

34/59

Charisma Carpenter

Issue: June 2004

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

35/59

Denise Richards

Issue: December 2004

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

36/59

Jenny McCarthy

Issue: January 2005

Jenny McCarthy went full bunny for her 2005 cover.

37/59

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

Issue: March 2005

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

39/59

Bai Ling

Issue: June 2005

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

40/59

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

Issue: March 2007

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

42/59

Amanda Beard

Issue: July 2007

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

43/59

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

Issue: December 2007

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

45/59

Anna Faris

Issue: September 2008

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

46/59

Carmen Electra

Issue: January 2009

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

47/59

Aubrey O'Day

Issue: March 2009

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

48/59

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

Issue: September 2009

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

50/59

Chelsea Handler

Issue: December 2009

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

51/59

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

Issue: March 2011

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

53/59

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

Issue: May 2011

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

55/59

Lizzy Jagger

Issue: June 2011

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

56/59

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

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

Issue: April 2015

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

59/59

Kylie Jenner

Issue: September 2019

Travis Scott took Kylie Jenner's 2019 Playboy cover.