The 15 Most Famous Playboy Playmates of All Time
Playboy magazine was an American institute. Established by Hugh Hefner in 1953 after a $1,000 loan from his mother, the men’s lifestyle publication quickly become well-known thanks to its cover girls. Each issue featured a cover girl known as a Playboy Playmate. These women would also feature as the magazine’s center-fold (either nude or semi-nude). Along with featuring famous Playmates, Playboy published short stories from a wide variety of authors and writers, interviews with public figures, and interesting articles you couldn’t find anywhere else. It played a big role in the sexual revolution and helped turn Hefner into a dressing gown-wearing celebrity.
Throughout its 47 year run, Playboy was involved in numerous controversies that only helped its popularity. The brand soon grew into Playboy Enterprises, Inc. and the iconic Playboy bunny logo was soon found on everything from t-shirts to mugs to bedsheets. Playboy magazine became a major part of pop culture and thrived in the 80s and 90s. But the introduction of the internet had a big impact on the magazine’s sales and the final issue was released in March 2020.
Over the course of its history, the magazine has featured hundreds of Playmates, including the likes of Marilyn Monroe, Monique St. Pierre, Shannon Tweed, Pamela Anderson, and Victoria Silvstedt. There has been everyone from movie stars and musicians to models and athletes. To celebrate the magazine’s legacy and all those who have featured in its pages, here are the 15 most famous Playboy Playmats of all time.
1. Pamela Anderson
Pamela Anderson holds the record for the most Playboy Playmate covers of all time, appearing center stage 13 times throughout the magazine’s life. Her first cover was in 1990 and it quickly made her a star. The following year she booked a gig on Home Improvement as Lisa and appeared for two seasons before hitting the big time with her role as Casey Jean “C.J.” Parker on Baywatch. Anderson was never far from the spotlight thanks to her many controversies (the sex tape with Tommy Lee) and six marriages to five men, but despite all this, she remained one of the most iconic Playmates of all time.
2. Jenny McCarthy
Similar to Anderson, Jenny McCarthy began her career as a model and featured on the cover of Playboy in 1993. Hugh Hefner selected her out of 10,000 applicants due to her “wholesome Catholic girl” look. She received a lot of backlash for the cover but was rewarded by Hefner with the title of Playmate of the Year in 1994 and a cool $100,000. She used this newfound fame to crack Hollywood, where she has had a semi-successful career, although her anti-vaccination ideology has put her at odds with many.
3. Marilyn Monroe
One of the biggest pop culture figures of all time appeared as the very first Playboy Playmate. Marilyn Monroe was the cover girl and centerfold of the very first Playboy released in December 1953. Taling with E! Online, Huge Hefner said she “kind of set the standard” as the “Sweetheart of the Month.” This would evolve into the Playmate of the Month. One surprising thing about her appearance in the magazine was that she never actually posed for Playboy, with the photos having been taken years earlier when Monroe was in need of quick cash.
4. Anna Nicole Smith
Similar to many women on this list, Anna Nicole Smith got her big break appearing on the cover of Playboy. The blonde Texan bombshell featured in the March 1992 edition of Playboy and was named Playmate of the Year in 1993. While she went on to have great success as a model, she never managed to crossover into movies and television, despite many years of trying. Along with her appearance in Playboy magazine, she was best known for marrying 86-year-old petroleum tycoon J. Howard Marshall. Many saw her as a gold digger, which impacted her career. She would struggle with drugs during the early 00s and sadly passed of an accidental overdose in 2007.
5. Dorothy Stratten
Canadian Dorothy Stratten was Playboy Playmate of the Month for August 1979 and Playmate of the Year in 1980. She also worked as a Bunny at the Playboy Club in Century City, Los Angeles. It’s believed Hefner was a big fan of her and thought she could have a successful film career. While she appeared in a couple of TV episodes and movies thanks to her Playboy cover, Stratten’s life was tragically cut short when her estranged husband murdered her before killing himself. She was just 20 years old.
6. Carmen Electra
It might be hard to believe but Carmen Electra got her start as a backup singer for Prince. She would go on to release one album (it bombed) before finding fame as a Playboy Playmate. Her first feature in the magazine was a nude pictorial in the May 1996 edition. To coincide with her joining hit series Baywatch in 1997, she once again appeared in the magazine. She would feature a further three more times–December 2000, April 2003, and the January 2009 anniversary issue–appearing on the cover for all three issues.
7. Barbi Benton
This one is a bit of a cheat. Despite gracing the cover of Playboy four times (July 1969, March 1970, May 1972, and December 1985), Barbi Benton was never actually crowned Playmate of the Month. Benton got her start as part of the entertainment show Playboy After Dark. She was quickly spotted by Hefner who took a liking to her. The two formed a relationship and dated for several years. She had a semi-successful entertainment career during the late 70s and early 80s before giving it all away to become a mum in 1986.
8. Kelly Monaco
Playboy and Baywatch seem to go hand in hand. Kelly Monaco was another Playmate who scored a role on the hit series. Before all that, the model sent a photo to Playboy in 1996 and promptly found herself on the cover of the magazine and named Playmate of the Year in 1997. She made numerous appearances in the magazine throughout the 90s and is best known these days for her role as Sam McCall on the soap opera General Hospital. She also won the first-ever season of Dancing with the Stars, which is not a bad feather in her cap.
9. Jennifer Jackson
Jennifer Jackson is notable for being the first African American Playboy Playmate. She featured as the centerfold of the 1965 edition of the magazine. She also worked as a Playboy Bunny in the Playboy Club during the 60s and her twin sister, Janis Jackson Holmes, was also a Playboy Bunny. Although she had the main spread in the March 1965 issue, she wasn’t the cover star. The first African American to achieve that feat was Darine Stern, who appeared on the cover of the October 1971 issue.
10. Kimberley Conrad
What makes this Playboy Playmate so special is the fact that she ended up marrying Hugh Hefner. Kimberly Conrad was Playboy‘s Playmate of the Month in January 1988 and became Playmate of the Year 1989, which was the same year she and Hef tied the knot. They were married for nine years and had two children, with Conrad turning the Playboy Mansion into more of a family-friendly venue. They separated in 1997 before finally divorcing in 2010 once the kids had grown up.
11. Victoria Silvstedt
Victoria Silvstedt has done it all. The Swedish model, actress, singer, and television personality is an all-around entertainment guru who caught the eye of Hugh Hefner in 1996. She wound up doing a photoshoot and being named the December 1996 Playmate of the Month. She was also chosen as the 1997 Playmate of the Year. While she went on to have great success as a model, securing the highly coveted Guess? contract, she continued to feature in a number of Playboy magazine special editions as well as Playboy Videos, music video type films featuring Playboy Playmates wearing little to no clothing.
12. Jayne Mansfield
Oozing sexuality, Jayne Mansfield was the perfect fit for Playboy Magazine. A struggling actor whose beauty (or bust) was getting in the way of her career, Mansfield posed for Playboy and instantly become a star. Not only did her February 1955 Playmate of the Month spread help boost her image, but also that of Playboy. She would go on to appear in the magazine regularly throughout the late 50s, modeling for the Playboy calendar and featuring in the 1955, 1956, 1957, 1958, and 1960 February issues of the magazine.
13. Ines Rau
Playboy broke down barriers with its November 2017 edition. The Playboy Playmate of the Month was Ines Rau, the magazine’s first openly transgender Playmate. While this caused a bit of controversy, it was applauded by many and demonstrated that Hef was more in tune with the times than many thought. She continues to model for big brand names around the world and advocate transgender rights.
14. Shannon Tweed
The wife of Kiss member Gene Simmons had a career just as successful as her make-up wearing boo. Shannon Tweed has starred in more than 60 films, although most fall in the erotic thriller category. Her appearance in Playboy actually came about thanks to the Canadian TV show Thrill of a Lifetime. This series granted regular people their wishes, with Tweed wanting to pose for Playboy. Hef obviously liked what he saw and Tweed was chosen as the Playmate of the Month for November 1981. She would then be named Playmate of the Year in 1982. She famously lived at the Playboy mansion for 14 months with Hefner. That is where she met Simmons. Tweed dumped Hef for the rock star and the rest is history.
15. Heather Rae Young
Heather Rae Young has gone from Playboy Playmate to real estate celebrity over the past 12 years. The former model made a name for herself when she was the Playboy Playmate of the Month for February 2010. While she dabbled in acting for a few years after, she eventually got her real estate license and turned her attention to selling homes.
She got another taste of fame when she was part of Netflix’s hugely successful real estate show Selling Sunset, which is currently filming its fifth season. Speaking about her time as a Playmate, she told UK tabloid The Sun; “It catapulted my career, it changed my life, it was the most defining moment in my life. I don’t regret anything I’ve ever done. I’m proud of my life. Everything I’ve done has got me to where I am today.”
See more about - A Peek At The Playboy Big Bunny Private Jet