1. Pamela Anderson (1989, 1991, 1992, 1993, 1994, 1996, 1997, 1998, 1999, 2001, 2004, 2007, 2011, 2016)
A Playboy cover record holder with 14 appearances, Pamela is every teen's favorite lifeguard and the ultimate muse of Malibu's beaches.
2. La Toya Jackson (1989, 1991)
Michael's older sister's decision to pose for Playboy caused an unprecedented sales frenzy in 1989. She did it once again in 1991, but just like her career as a singer, her success didn't last long.
3. Coco Austin (2008)
Coco was born to be a bunny without a doubt and her staggering pictorial for Playboy in 2008 made the whole world to be jealous of Ice-T.
4. Carmen Electra (2003, 2009)
Carmen achieved fame for her comic roles in parody films such as Scary Movie, but her pictorials for Playboy in 2003 and 2009 aroused other feelings much more intense than mere giggles.
5. Jenny McCarthy (1994, 1996, 1997, 2005, 2012)
Playmate of the Year in 1994, Jenny emerged from Playboy's own pages to become a celebrity. She later reappeared in Playboy several times.
6. Sable (1999, 1999, 2004)
WWE wrestler Rena Mero aka Sable knocked out the entire world when she posed naked twice in 1999. She later posed one last time in 2004.
7. Farrah Fawcett (1995, 1997)
It took more than two decades to this Charlie Angel finally yield to countless requests and pose nude for Playboy, which only happened in 1995 when she was already a 48-year-old woman. As a result of the huge amount of sales of her first appearance, she later showed up again in 1997.
8. Diora Baird (2005)
This former model for Guess tried a career in Hollywood that didn't take off as she intended, on the other hand her Playboy pictorial in 2005 was undeniably a memorable one.
9. Kim Kardashian (2007)
If being in the spotlight is what Kim's life is all about, it's no surprise at all when she took off her clothes for Playboy in 2007. And it was no surprise at all that her magazine quickly sold out.
10. Kelly Brook (2010)
Despite not being a member of royalty, this british model and media peronality is a true beauty queen coming from UK as we could see in detail in 2010.
11. Tara Reid (2009)
A legion of fans rushed to newsstands in 2009 to buy Tara's magazine, the muse of the time when they were still goofy teenage virgins.
12. Joanna Krupa (2005, 2009)
Already a veteran of others men's magazines such as Maxim and FHC, Joanna undressed in 2005 and 2009 for Playboy. And let's face it, being an animal rights activist it would be very wrong for Joanna to refuse to be a bunny.
13. Kristy Swanson (2002)
The original vampire slayer made all Buffy's fans dream come true when she posed naked in 2002, stealing back all the attetion from Sarah Michelle Gellar.
14. Denise Richards (2004)
When Denise decided to get naked for Playboy in 2004 it wasn't even close to be the wildest thing she'd done in her life until that moment as she'd already married Charlie Sheen two years before.
15. Charisma Carpenter (2004)
Charisma transited through several tv shows in the late 90s and early 2000s without ever reaching stardom, nonetheless she shone brighter than all her past co-workers together in her pictorial for Playboy in 2004.
16. Garcelle Bouvais (2007)
Ebony goddess Garcelle Bouvais wasn't just the love interest of Jamie Foxx (in his tv show) but also the entire male audience, so imagine how thrilled all her fans were when she posed naked in 2007
17. Cindy Crawford (1988, 1996, 1998)
One of the most beautiful and desired woman of the 80's, Cindy was the first supermodel to ever agree to pose nude for Playboy in 1988. Later she did it again in 1996 and 1998.
18. Elle Macpherson (1994)
This supermodel was nicknamed "The Body" because of her perfect measurements, and luckily for us Playboy could capture the remainder of its as-yet-unknown measurements in 1994.
19. Vida Guerra (2006)
FHM Model of the Year in 2004, this sexy cuban glamour model successfully migrated to Playboy's pages in 2006, when the whole world could finally contemplate all her beauty uncensored.
20. Rachel Hunter (2004)
This supermodel initially teased us posing as swimsuit model for Sports Illustrated in 1989, but in 2004 she finally showed every inch of her perfect body in the pages of Playboy.
21. Kiana Tom (2002)
When this fitness expert decided to get naked in 2002 she encouraged a different type of exercise than the ones she used to teach on her very popular exercise program on ESPN.
22. Lindsay Lohan (2012)
Lindsay's career definitely had its ups and downs, however this eternal mean girl did not disappoint when she made a glamorous tribute to Marilyn Monroe in 2012.
23. Barbara Carrera (1982)
Luckily for us this Nicaraguan bond girl avoided saying never and agreed to pose nude in 1982.
24. Raquel Welch (1979)
Probably many years before even your father was born, Raquel was huge sex-symbol during the 60's and 70's and the best part of it is that she was not ashamed to pose for Playboy in 1979.
25. Charlize Theron (1999)
At the very begginig of her career in Hollywood, Charlize did pose nude for Playboy in 1999. But as we could see with the follow-up of her career, getting naked was never an obstacle for slim blondie.
26. Tricia Helfer (2007)
The geek world was thrown into complete madness when this hot cylon decided to strip naked for Playboy in 2007.
27. Winter Zoli (2011)
Zoli promoted waves of anarchy among her fans when her naked pictures were published in 2011 by Playboy magazine.
28. Traci Bingham (1998)
Being rescued by one of the Baywatch girls was every man's dream in the 90's, but Bingham's naked pictures for Playboy in 1998 were more than enough.
29. Naomi Campbell (1999)
Naomi was one of the most requested supermodels in the 90's and thankfully for us didn't say no to Plaboy in the Christmas of 1999.
30. Sharon Stone (1990, 1992)
This femme fatale appeared twice in the pages of Playboy, first in 1990 and then in 1992 after the role that changed Sharon's career forever.
31. Amanda Beard (2007)
Amanda was already breathtaking to watch while competing in the Olympic pools, so imagine how grasping her fans were when she finally agreed to pose nude in 2007.
32. Stephanie Seymour (1991, 1993)
Do you remember the delightful woman who used to appear in some of the Guns N' Roses clips? Well that was supermodel Stephanie Seymour who posed naked for Playboy in 1991 and 1993.
33. Daryl Hannah (2003)
Daryl was a long forgotten actress from the 80's when Tarantino pulled her back into the spotlight. Taking advantage of her rebirth, she didn't turn down Playboy's invitation in 2003.
34. Kim Basinger (1983)
Few years before her role in the erotic movie 9 1/2 Weeks, Basinger had already posed nude in 1983.
35. Stacey Dash (2006)
Stacy never gave us any clue that one day she would pose naked for Playboy, as it surprisingly happened in 2006.
36. Arianny Celeste (2010)
Luckily the beauty of Arianny was not restricted to the UFC rings, as the alluring ring girl showed her nudity in the pages of playboy in 2010.
37. Lizzy Jagger (2011)
Life is full of twists, isn't it? That's what rockstar Mick Jagger bitterly find out when his daughter posed nude for Playboy in 2011.
38. Aubrey O'Day (2009)
Once a member of a girl band, Aubrey decided to flight solo in her musical career and also inside the pages of Playboy as we could see in her solo pictorial in 2009.
39. Drew Barrymore (1995)
Anyone who only knows the settle Hollywood actress of today won't believe that Drew was a total wreck during the 90's, so much that she was only nineteen she when appeared naked in the pages of Playboy in 1995.
40. Shannen Doherty (1994, 2003)
Did you fell in love for lovely Brenda Walsh in the 90's? If so I bet you took a peek at her sexy pics for Playboy in 1994 and later in 2003.