Playmates For A Day! The 45 Sexiest Celebrities To Have Appeared In Playboy
Apr. 20 2019, Updated 11:06 p.m. ET
Playboy Magazine has been home to some of the sexiest centerfolds over the years. And while readers (not that any reading actually happens) have always enjoyed glancing at some of Hugh Hefner's sexiest bunnies over the years, the basic Playboy spread was nothing compared to those special issues that featured some of the hottest celebrities Hollywood had to offer. Celebrity Playboy issues were something special, and RadarOnline.com has collected the 45 sexiest celebs to have graced the pages of the world famous magazine.
Hef wasn't always successful in convincing celebs to pose for his mag. Celebrities including, Jennifer Aniston, Katy Perry, Lady Gaga, Mel B and Patti Mallette kindly refused. But he was successful many times throughout his storied career. From Kim Kardashian to Drew Barrymore, Hef had himself 45 of the hottest, most famous faces join his world and become playmates for a day.
1. Kim Kardashian
Kim Kardashian has made a career out of scandalous magazine spreads. It was only natural that she would appear in the most famous nude mag of them all. The Keeping Up with The Kardashians star graced the pages of Playboy Magazine in 2007.
2. Drew Barrymore
Drew Barrymore turned her life around in the '90s but she still had some wild in her to let loose. The actress chose to show off some skin in 1995 when she appeared on the cover of Playboy.
3. Charlize Theron
Charlize Theron found herself on the cover of an issue in 1999, prior to her days as an Oscar-winning actress and blockbuster headliner.
4. Pamela Anderson
Pamela Anderson and Playboy were virtually synonymous for a time. The Baywatch actress has appeared on the cover of Playboy more times than anyone else in the magazine's storied history. Beginning in 1989, Anderson has appeared on 13 different covers, easily cementing her as Hugh's favorite go-to girl.
5. Chelsea Handler
Chelsea Handler has never shied away from showing off some skin. The outspoken comedian did just that for Playboy's 2009 Christmas issue.
6. Mariah Carey
Mariah Carey made an appearance in 2007. While she she didn't go completely nude, Carey showed off plenty of skin.
7. Madonna
Madonna's entire persona has revolved around embracing her sexuality. So it was no surprise when she decided to pose for the cover of Playboy in 1985 after the magazine published a collection of nude photos before she began her music career.
8. Marilyn Monroe
Marilyn Monroe put Playboy on the map with one of the most iconic photo shoots of all time. In 1953, the magazine's very first issue and centerfold featured the young actress in a series of previously published nude photographs.
9. Lindsay Lohan
Lindsay Lohan has always managed to snag headlines despite a waning film-career. One of her most memorable moments was when she posed for Playboy in 2011, in an editorial mirroring Marilyn Monroe's final nude photo session.
10. Olivia Munn
Before she was starring in films, OIivia Munn was working her way into the business as a television host and was the desire of gamers all over the world. Playboy knew this, and decided to have Munn grace their cover in 2009.
11. Jessica Alba
Jessica Alba's appearance on the cover of Playboy in 2006 was surprising to everyone...including Alba herself. Unfortunately, Playboy published her photo for the cover without her knowledge after the actress refused to appear in a photo shoot for the magazine. Luckily, Hef himself wrote her a personal apology which she accepted.
12. Paris Hilton
OK, so Hef wasn't exactly forthright when it came to some of Playboy's cover-girls. Like Alba and Monroe before her, Paris Hilton found herself on the cover the magazine in 2005 without her approval. Luckily, her friendship with Hefner was enough to let bygones be bygones.
13. Shannen Doherty
Shannen Doherty may have been the good girl on-camera, but off-camera was an entirely different story. The notorious actress posed nude for Playboy in 1993 prior to her leaving Beverly Hills, 90210.
14. Sharon Stone
Sharon Stone appeared twice on the cover of Playboy. She first appeared in 1990 to promote Total Recall, two years before baring it all once again for the Christmas issue in 1992—hot off the heels of her infamous leg-crossing scene in Basic Instinct.
15. Anna Faris
It would have been odd if Anna Faris hadn't posed for the magazine in 2008, when she was promoting The House Bunny—a film in which she played a Playboy Bunny.
16. Jenny McCarthy
Jenny McCarthy actually began her career as a Playboy Playmate in 1993. In fact, she was named Playmate of the Year in 1994 before before segueing into film and television.
17. Azealia Banks
Azealia Banks' 2015 photo shoot was appropriately revealing. The outspoken and controversial rapper posed in a pink paddling pool while pouring milk over her naked body. Her interview was just as raunchy as she discussed her past sexual encounters.
18. Carmen Electra
Carmen Electra was a regular for the magazine, appearing in five different issues since 1996.
19. Denise Richards
Denise Richards made waves when she posed for an issue a mere five months after giving birth. Post-baby body for the win!
20. Brooke Shields
Brooke Shields already had years of modeling experience before she made the cover of Playboy at age 21 in 1986.
21. Geri Halliwell
Geri Halliwell, AKA Ginger Spice was yet another celebrity to end up in Playboy without actually knowing about it. The former Spice Girl's early work as a nude model resurfaced for a 1998 issue, shortly before leaving the pop group.
22. Dita Von Teese
Dita Von Teese was an obvious choice to be on the cover of Playboy in 2002. The burlesque performer has always been in touch with her sexuality and was more than willing to join the long list of celebrities to feature in the magazine.
23. Kate Moss
Kate Moss certainly made a statement for the magazine's 60th anniversary. The supermodel graced the cover wearing the iconic bunny outfit for a mammoth 18-page spread.
24. Naomi Campbell
Fellow supermodel, Naomi Campbell had posed for the magazine in 1999 for a stylishly sexy 14 page spread.
25. Kim Basinger
Before Kim Basinger broke out as a Bond girl in Never Say Never Again, she bared down for a nude pictorial in 1981. The sultry photos weren't used for another two years however.
26. Goldie Hawn
Goldie Hawn was everywhere in the '80s and that included the pages of Playboy. The Oscar-winning actress appeared on the cover in 1985.
28. Latoya Jackson
Michael Jackson's older sister, Latoya Jackson appeared in what was one of the highest selling issues of all time in 1989.
29. Stacy Dash
While she didn't make the cover, actress and television personality Stacy Dash appeared nude for a 2006 issue. It was definitely an eye-opening layout for fans of the Clueless star.
30. Charisma Carpenter
Fans of Angel and Buffy the Vampire Slayer were in for a tantalizing treat when Charisma Carpenter disrobed for a pictorial in 2004.
31. Aubrey O'day
Amid Danity Kane's breakup, singer Aubrey O'Day strayed from the group and showed the world just how wild she was by posing nude for Playboy in 2009.
32. Jerry Hall
Supermodel and Mick Jagger's former partner, Jerry Hall, stripped down for Playboy in 1985. However, this wouldn't be the last time someone close to Jagger would appear in the magazine.
33. Lizzy Jagger
Lizzy Jagger followed in her mother's footsteps over 20 years later when she landed the cover of Playboy in 2011. Jagger and Hall's supermodel daughter expressed herself as only the child of a rock legend could.
34. Elle Macpherson
Elle Macpherson was known as "The Body" during her modeling heyday. Of course this meant that nude photos of the statuesque model would be in high demand. While she was no stranger to baring it all after appearing nude in the film, Sirens, Macpherson decided that if fans were going to see her naked again, it'd be on her own terms. That was exactly why she decided to pose for Playboy in 1994.
35. Cindy Crawford
Like Macpherson, nude photos of Cindy Crawford were in demand in the '90s. Crawford ditched the runway for a centerfold when she posed nude for Playboy in 1996 and once again in 1998.
36. Farrah Fawcett
Farrah Fawcett had appeared on the cover of Playboy in 1978, but she wouldn't appear nude until 1995 when the iconic sex symbol was 48! She appeared once more in 1997, showing the world that age was nothing but a number to her.
37. Ursula Andress
Some actresses may have posed for Playboy to make a statement about sexuality or to promote their work, but former Bond girl Ursula Andress had a much simpler reason when she was asked why she chose to pose nude: "Because I'm beautiful."
38. Jaime Pressly
Actress and Margot Robbie look-alike, Jaime Pressly embraced her naked self when she posed for Hef in 2004.
39. Heidi Montag
Heidi Montag took part in a semi-nude photo shoot for the magazine in 2004. While she didn't go full-frontal, the former reality star wowed readers with her seductive look.
40. Tara Reid
Normally you'd be able to see Tara Reid naked by accident. But in 2014, she decided to disrobe on purpose when she posed for Playboy. Take that, nip slips!
41. Taryn Manning
Taryn Manning became a Playboy cover girl when she posed for a sex and music issue in 2011. The actress and singer/songwriter was looking fierce and confident as she posed for the revealing pictorial.
42. Karina Smirnoff
Karina Smirnoff of Dancing with the Stars did more than just show off her moves when she posed nude in 2011.
43. Tricia Helfer
Tricia Helfer made many fantasies come true when she posed nude in 2007. The former Battlestar Galactica actress was seen like never before, much to the shock of her fans.
44. Vanna White
Before Wheel of Fortune, Vanna White was just an aspiring model looking to pay her rent. It was that need that led to her posing nude earlier in her career. Naturally, the demand for those photos went up after she made it big, leading to Hef purchasing those photos and putting White on the cover in 1987
45. Bai Ling
The force was strong with Bai Ling as she posed nude for a Star Wars-inspired issue in 2005.
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