Playboy launched in December 1953 with a celebrity on the cover and in the pages Marilyn Monroe.
Around the turn of the ’80s, that changed. Playboy got hip to the value of naked famous ladies. Pictorials by Bo Derek, Barbara Carrera, and Kim Basinger were some of the earliest examples of celebrities who decided to “do Playboy” a phrase that is now a ubiquitous suggestion for every starlet with a movie or two under her belt. By the late ’90s, Playboy was full-on addicted to celebrities.
How do you pick the best from such an amazing group? It wasn’t easy. The formula was based on beauty and x-factor as well as celebrity status. Celebrity status didn’t always help you, though.
Here are the hottest Playboy Playmates of all time.
20. Marilyn Monroe
Marilyn Monroe was an American actress, model, and singer. Famous for playing comic “blonde bombshell” characters, she became one of the most popular sex symbols of the 1950s and was emblematic of the era’s attitudes towards sexuality.
19. Jenny McCarthy
Jennifer Ann McCarthy, sometimes credited as Jenny Wahlberg, is an American anti-vaccine activist, actress, model, television host, author, and screenwriter. She began her career in 1993 as a nude model for Playboy magazine and was later named their Playmate of the Year.
18. Carmen Electra
Tara Leigh Patrick, better known by her stage name Carmen Electra, is an American glamour model, actress, television personality, singer, and dancer. She began her career as a singer after moving to Minneapolis, Minnesota, where she met Prince, who produced her debut record.
17. Kayla Garvin
Kayla Garvin’s view on her career, “I never planned on modeling. I always knew, whatever I did, I wanted to be artistic in some way.” Kayla Garvin did major in psychology with a minor in art.
16. Cindy Crawford
Cynthia Ann Crawford is an American model and actress. Her years of success at modeling made her an international celebrity that has led to roles in television and film, and work as a spokesperson.
15. Elle Macpherson
Eleanor Nancy Macpherson is an Australian model, businesswoman, television host and actress. She is known for her record five cover appearances for the Sports Illustrated Swimsuit Issue beginning in the 1980s, leading to her nickname “The Body”, coined by Time in 1989.
14. Barbara Carrera
Barbara Carrera is a Nicaraguan American film and television actress and former model. She is known for her roles as SPECTRE assassin Fatima Blush in Never Say Never Again, as Natalia Rambova in Condorman, and as Angelica Nero on the soap opera Dallas.
13. Rachel Hunter
Rachel Hunter is a New Zealand Supermodel, actress and the host of Imagination Television’s Rachel Hunter’s Tour of Beauty. She has appeared on several magazine covers, including Vogue, Elle, Rolling Stone, Sports Illustrated, Playboy, Cosmopolitan and Harper’s Bazaar.
12. Stacey Dash
Stacey Lauretta Dash is an American actress and former talk show host. Dash is known for her co–starring role as Dionne Marie Davenport in the 1995 feature film Clueless and its eponymous television series. She has also appeared in films such as Moving, Mo’ Money, Renaissance Man, and View from the Top.
11. Shannon Tweet
Shannon Lee Tweed Simmons is a Canadian actress and model. One of the most successful actresses of mainstream erotica, she is identified with the genre of the erotic thriller.
10. Kate Moss
Katherine Ann Moss is an English model and businesswoman. Born in Croydon, Greater London, she was discovered in 1988 at age 14 by Sarah Doukas, founder of Storm Model Management, at JFK Airport in New York City.
9. Ursula Andress
Ursula Andress is a Swiss film and television actress, former model and sex symbol, who has appeared in American, British and Italian films. She is best known for her breakthrough role as Bond girl Honey Ryder in the first James Bond film, Dr. No. She later starred as Vesper Lynd in the James Bond film Casino Royale.
8. Sharon Stone
Sharon Vonne Stone is an American actress, producer, and former fashion model. After modelling in television commercials and print advertisements, she made her film debut as an extra in Woody Allen’s comedy-drama Stardust Memories.
7. Kim Bassenger
Kimila Ann Basinger is an American actress, singer and former fashion model. Following a successful modeling career in New York during the 1970s, Basinger moved to Los Angeles where she began her acting career on television in 1976.
6. Drew Barrymore
Drew was just 19 when she posed for Playboy, but she’d already lived a rock-star life. And not the good kind of rock-star life—she was going to Studio 54 and doing coke as a pre-teen. She got her shit together, though, and today is a bankable star, but in 1995 she was still a wild child. It was around this time, you may recall, that she flashed birthday boy David Letterman on his talk show.
5. Dita Von Teese
Dita Von Teese is an American vedette, burlesque dancer, model, costume designer, entrepreneur, singer, and actress. She is credited with re-popularizing burlesque performance, earning the moniker “Queen of Burlesque”
4. Bo Derek
Bo Derek is an American film and television actress, film producer, and model perhaps best known for her breakthrough role in the 1979 film 10. The film also launched a bestselling poster for Derek in a swimsuit, and subsequently she became one of the most popular sex symbols of the 1980s.
3. Lindsay Lohan
Lindsay Dee Lohan is an American actress, businesswoman, fashion designer, and singer. Born and raised in New York, Lohan was signed to Ford Models as a child. Having appeared as a regular on the television soap opera Another World at age 10, her breakthrough came in the Walt Disney Pictures film The Parent Trap.
2. Denise Richards
Denise Lee Richards is an American actress and former fashion model. She has appeared in numerous films, including Starship Troopers, Wild Things, Drop Dead Gorgeous, The World Is Not Enough as Bond girl Christmas Jones, Valentine, and Undercover Brother.
1. Pamela Anderson
Blonde bombshell Anderson has been posing for Playboy for three decades. She’s also been on more covers for the magazine than any other person, so picking one was a challenge and a privilege. Her tongue-in-cheek January 2007 shoot (pictured above) pretty much epitomizes her relationship with the brand.
Issue: October 1989, February 1991, July 1992, August 1993, November 1994, January 1996, September 1997, June 1998, February 1999, July 2001, May 2004, January 2007, January 2011
Which gorgeous Playmates didn’t make the list? Hiromi Oshima was one of the few blondes that caught the eye of Hugh Hefner, that’s enough for an honorable mention. How about Robin Givens, remember her? She was Mike Tyson’s sweetheart and then she wasn’t. Kim Kardashian did Playboy after her sex tape. It may be cold in Canada, but they do make great looking blondes; Jayde Nicole was a prime example of that! Finally, Jayne Mansfield graced the cover and pages of Playboy in 1963. She was the definition of sexy during her time and was Miss February in 1955. She didn’t make the list, which tells you how competitive this group is.
