Women You Didn't Know Were in Playboy

Some of these celebrities would rather forget their Playmate pasts.
ILLUSTRATOR Jasrelle Serrano

Of all the many things the late, great Hugh Hefner has said and done—and there have been many, as befits a nonagenarian tycoon like Hef—the invention of the Playboy Playmate is arguably just as famous as Playboy magazine itself.

The Playmate, of course, is the centerfold model featured in every issue; not to be confused with the Playboy Bunnies, who were the waitresses in Playboy Clubs in the US, and were iconically clad in the trademark bunny suit. There have been a number of famous women who’ve been able to list their experience as a Playboy Bunny in their CVs (including Debbie Harry, Lauren Hutton, Dorothy Stratten), but those who became Playmates were a more rarefied bunch, most of them appearing in the magazine on their way to being top models.

The magazine’s cover subjects were another club altogether, often featuring celebrities at the peak of their careers. Though a few of them have said that they regretted being in Playboy, the vast majority have enjoyed the attention and the wave of popularity that helped their careers.


Drew Barrymore (cover, January 1995)
Few people still think of Barrymore as that cute little kid in E.T., but back in the mid-‘90s, she was still struggling to break free of that image. She agreed to pose nude for Playboy in 1995, appearing in one of the most controversial covers of that time. E.T. director (and Barrymore’s godfather) famously sent her a blanket following the issue’s publication, with a note that read, “Cover yourself up.”


Katarina Witt (cover, December 1998)
Legendary ice skater Katarina Witt was already four years out of her last Olympic performance when she appeared on the cover, but she was determined to destroy the image of ice skaters as “cute, pretty ice princesses.” The cover was also the second issue to ever sell out; the first one was the magazine’s inaugural issue, featuring Marilyn Monroe.


Charlize Theron (cover, May 1999)
The revealing photographs of the acclaimed actress came out when Theron was already a rising young star with movies like The Devil’s Advocate and The Cider House Rules under her belt. In fact, she’d just landed the cover of Vanity Fair a few months before the May 1999 Playboy cover. The photographs were taken a few years before, however, when Theron was still an unknown model, and she has since said that she never meant for the photos to be published, and that she regrets the appearance in the magazine.

Marilyn Monroe (cover, December 1953 inaugural issue)
Hefner has attributed the success of Playboy to his choice for the magazine’s first cover subject, because there was no bigger star then or since. The inaugural issue not only had Marilyn Monroe on the cover; it also featured nude photos of her inside. Auspiciously for Hefner, the print run of about 50,000 copies sold out. Monroe, however, never agreed to pose for the magazine: The photos were taken in 1949 by photographer Tom Kelley, and sold to a company that made calendars. For that initial shoot, Monroe was paid only $50.

Monroe had no hard feelings about the publication of the photos, though, and reportedly became friends with Hefner. (In a surprising turn of events, it looks like Hefner will be interred next to Monroe, as he bought the vault next to her grave in 1992.)


Jayne Mansfield (February 1955)
Jayne Mansfield was known for being the first actress to appear topless in mainstream films in the 1960s, but it was her early appearances as a Playmate—the first one was in February 1955—that really made her reputation as a bombshell. She continued to appear in the magazine up until she died in a car accident at the age of 34.


Kim Kardashian (December 2007)
Okay, so it may have been more surprising if the Kardashians managed to keep themselves out of Playboy, but coming up on the tenth anniversary of both their show and of Kim’s cover, it might bear bringing up again. In fact, Kim was among the celebrities who led tributes to Hugh Hefner on social media.


Tetchie Agbayani (German edition, cover, July 1982)
The 1979 Mutya ng Pilipinas enjoyed a busy career in the Philippines after her pageant win, becoming an actress and a model who didn’t shy away from showing a little skin. Still, jaws dropped when the actress appeared on the cover of the German edition of the magazine in 1982 (and then later in a special US edition featuring Women of the World). The bold move helped launch Agbayani’s career internationally, and she appeared in several Hollywood movies afterward, including the critically acclaimed The Emerald Forest.

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