22 Celebrities Who Posed for Playboy

Playboy is one of America’s most recognizable brands. Started by the late Hugh Hefner after a $1,000 loan from his mother, the men’s lifestyle magazine became one of the biggest and most successful publications the world has ever seen. Containing interviews with celebrities and stories from famous authors and journalists, the big seller was the nude centerfold in the middle of the magazine. Along with models, many celebrities who posed for Playboy gained more exposure and fans from appearing naked in the mag. 

The magazine played a huge role in the sexual revolution of the 60s and helped sex become more acceptable in mainstream society. It turned Hefner into some sort of sexual male role model for men (yuck), with Playboy Enterprises, Inc. turning into a multi-million dollar business. But as the saying goes, “all good things come to an end.”

With the rise of the internet, the accessibility to pornographic material with just the click of a button, and people’s view on the sexualization of women, Playboy’s readership dropped dramatically in the 21st century. It tried getting with the times by ditching the nudity but that didn’t work, and Playboy’s final issue hit the shelves in 2020.

While it may be gone, Playboy is not forgotten. The magazine helped launch the career of many up-and-coming models and cemented many celebrities as sex symbols. There have been so many famous faces on the cover you might have forgotten some of the biggest, so here are 22 of our favorites. 

22 Celebrities Who Posed for Playboy

1. Marilyn Monroe

One of the most famous women to appear on the cover of Playboy was actress Marilyn Monroe. The blonde bombshell was on the inaugural issue of Playboy magazine. Interestingly enough, the photo chosen as the centerfold was actually taken from a calendar Marilyn Monroe posed for. 

2. Pamela Anderson

Pamela Anderson first appeared in the pages of Playboy magazine’s October 1989 issue. The exposure helped her get the role of Lisa on Home Improvement, which led to her most famous gig playing Casey Jean “C.J.” Parker on Baywatch.

Andreson went on to have the most cover appearances of all time, popping up in the magazine 13 times over a period of 22 years. When it came to Hugh’s favorite Playboy playmate, Anderson was certainly at the top of the list. 

3. Lindsay Lohan

Troubled star Lindsay Lohan was handed a lifeline in 2012 when she got the chance to model for Playboy. Coming off some legal issues, Lindsay Lohan’s shoot was inspired by Marylin Monroe, with the normally red-haired actress sporting lush blonde locks. The photos are quite provocative but tastefully done and gave Lohan a boost in popularity. 

4. Drew Barrymore

The mid-90s weren’t kind to Drew Barrymore’s career. She starred in a series of underperforming movies and let her private life take center stage, with her wild personality becoming more interesting than her movie roles. This led to Barrymore appearing in a 1995 issue of Playboy. The images were well received and the issue sold really well, although not everyone was excited.

Her godfather, Steven Spielberg, gifted her a quilt for her 20th birthday with a message that read, “Cover yourself up.” Inside the rug was the images from her photo shoot digitally edited to show Barrymore wearing clothes. 

5. Anna Nicole Smith

Playboy helped kickstart Anna Nicole Smith’s career. She first graced the cover of the March 1992 edition of Playboy and was then named Playmate of the Year in 1993. This helped Smith gain several modeling contracts and crossover into the entertainment industry, although she struggled to find success as an actress. 

Unfortunately, Smith struggled with her time in the spotlight and passed away from an accidental overdose aged 39 in 2007.

6. Cindy Crawford

When it comes to supermodels, Cindy Crawford will go down as one of the greats. She was everywhere in the 80s and 90s, modeling for all the big fashion brands around the world. She also appeared in two issues of Playboy in 1988, with both shot by famed photographer Herb Ritts. 

7. Kim Kardashian

At the beginning of her reality TV career, Kim Kardashian got the chance to pose for Playboy. Although a little nervous, her mom suggested it would be good for her profile, so Kardashian went through with the shoot. Her issue came out in 2007 and was well-received by readers.

That said, Kim Kardashian now regrets posing for the magazine. “I’m sorry I did Playboy. I was uncomfortable,” she said in an interview with Harper’s Bazaar. 

8. Dolly Parton

Unless you were an avid reader of Playboy, you might not know that country singer Dolly Parton graced the magazine’s pages. Parton appeared on the October 1978 cover wearing the famous Playboy bunny ears. Unlike most cover stars, Parton didn’t get her kit off, instead posing in a tasteful one-piece. 

9. Kim Basinger

At the beginning of her career, the beautiful Kim Basinger posed in the magazine’s February 1983 issue. Basinger actually posed for the photos in 1981, but it took a couple of years before the images appeared in Playboy.

The magazine was used to promote the Bond film Never Say Never Again, in which Basinger co-starred in with Sean Connery. Her nude centerfold helped Basinger secure better roles and boosted her profile in Hollywood. 

10. Jenny McCarthy

Jenny McCarthy caused controversy in her neighborhood when getting nude for Playboy. At the age of 21, she was offered $20,000 to appear in Playboy. Happy to accept the money, McCarthy posed for the October issue and went on to become Playmate of the Month for October 1993.

Hugh Hefner believed she had a “wholesome Catholic girl” appeal, and the shoot featured McCarthy in schoolgirl attire. This didn’t go down well with her conservative family, who lectured her about the eternal damnation in hell that awaited her if she continued down this path of sin. 

Thankfully McCarthy didn’t listen. After being awarded Playmate of the Year (1993) and paid a $100,000 salary, she soon found herself in Hollywood rubbing shoulders with all the big players, with Playboy kick-starting her career in the entertainment world. 

11. Naomi Campbell

After years of strutting her stuff on catwalks and appearing in dozens of commercials, Naomi Campbell changed things up by appearing nude in Playboy. She disrobed for the December Christmas issue in 1999. It was one of her last big modeling gigs, with Campbell falling out of favor with critics during the 00s. 

12. Goldie Hawn

In 1985, at the age of 39, Goldie Hawn stripped off for Playboy. The iconic cover featured Hawn posing in a giant glass, with the issue also containing an interview with the star of Wildcats and Overboard. 

13. Madonna 

Madonna’s appearance in Playboy is controversial. She didn’t actually pose for the photos. Playboy and competitor Penhouse came into possession of nude photos taken of Madonna when she worked as an art model in 1978. Both publications released the photos without Madonna’s consent, although Madge didn’t seem bothered by the commotion. 

14. Charisma Carpenter

Best known for her roles in Buffy the Vampire Slayer, Angel, Veronica Mars, and Surviving Evil, Charisma Carpenter has also been a Playboy cover girl. Carpenter’s ten-page spread can be found in the June 2004 issue of Playboy magazine. When asked by People if she would ever do Playboy again, Carpenter had this to say: 

“I don’t know. I did Playboy for a very specific reason. Not only was it a good financial move, but it was about the place I was at in my life. I had just had my son and I’d gained 50 pounds during pregnancy. I wanted to get back to my old self. I wanted to feel desirable and sexy. So I thought, ‘What if I went full throttle’?”

15. Karina Smirnoff

Another celebrity who happily got naked for Playboy was Karina Smirnoff. The Soviet-born American has won countless competitions and has been a mainstay of Dancing With the Stars over the years. She got naked for the May 2011 issue at the age of 33.

“As a dancer, I’ve always embraced my body. I’m thrilled to show off my strong, toned physique in the pages of Playboy and celebrate my sexiness,” she told the Daily Mail. “To me, sexy is the confident energy a person produces. Sexy is the comfortable feeling of being who you are. Sexy is not just having beautiful lips, legs, and arms; it’s beyond that. Sexy is soul.”

16. Paris Hilton 

It was inevitable that Paris Hilton would end up on the cover of Playboy at some stage in her life. After being involved in a sex tape (although not her idea for it to go viral) and finding fame for not really doing anything, taking her clothes off for a bucket load of cash seemed like an easy career decision. You can check her out in the March 1995 edition. 

17. Kate Moss

Famed model Kate Moss finally appeared on the cover of Playboy for the magazine’s 60th-anniversary celebrations. Posing in the famous Playboy bunny ears and suit, Moss is a vision. The 18-page shoot was captured by Mert Alas and Marcus Piggott and captures the then soon-to-be 40-year-old Moss in all her beauty, both clothed and non-clothed. 

18. Bo Derek 

Bo Derek had a good relationship with Hugh Hefner and Playboy. Her first cover was in 1980, a 12-page spread for the March issue shot by her husband John, who was worryingly 45 years older than her (they surprisingly stayed together until his death from heart problems).

Derek would once again rock the pages later in the same year before coming back for issues in 1981, 1984, and 1994.

19. Farrah Fawcett

As the star of Charlie’s Angeles season one and one of the main characters in The Six Million Dollar Man, Farrah Fawcett had people up in arms when she posed semi-nude in the December 1995 issue of Playboy. The reason being people were flabbergasted that a celebrity her age (48) would pose nude. 

Fawcett obviously didn’t give two shits, as she returned on the Playboy cover two years later at age 50 for a full nude spread. The July 1997 issue was one of Playboy’s best-selling and demonstrated age was no barrier when it comes to appreciating beauty.

20. Carmen Electra 

First appearing in a nude pictorial for Playboy magazine’s May 1996 issue, Carmen Electra would return several times over the intervening years. Moving to Los Angeles and scoring a role on Baywatch, Electra showed off her body in a further four issues; June 1997, December 2000, April 2003, and January 2009. She was the cover star in 2000, 2003, and 2009.

21. Mariah Carey

Mariah Carey was another celebrity who got a photo spread in Playboy but managed to keep her clothes on. Her appearance came in the March 2007 issue and was used to help promote the release of her album E=MC², which ended up being a critical and commercial success. 

22. Elle Macpherson

When it comes to iconic Playboy covers, look no further than when Elle Macpherson appeared as the magazine’s centerfold. The Australian model oozed sexuality as she sits with her legs crossed and gazes into your eyes. Phew! 

Macpherson’s decision to pose nude was due to the media digging around to find risque photos of her after she got naked in the 1994 film Sirens. Paparazzi were apparently contacting her ex-boyfriends for nude pics, so Macpherson decided to cut them off at the path and pose nude of her own volition, resulting in the incredible 1994 Playboy shoot.