Nancy Sinatra — daughter of crooner Frank Sinatra, Lee Hazlewood collaborator, and “These Boots Are Made for Walkin'” hitmaker — wore her best boots and not much else for a 1995 Playboy spread. The singer was 54, which caused controversy amongst fans. Nancy discusses her feelings about posing in this clip from Geraldo Rivera.
Dynasty villainess and author Joan Collins took it off for Playboy at the age of 50. The English actress was photographed by George Hurrell, known for his glamorous portraits of classic Hollywood stars from the ‘30s and ‘40s. Playboy interviewed the actress at age 52, which you can watch in the below clip.
While it’s hardly surprising that Dita Von Teese posed nude, the burlesque performer and fashion entrepreneur is associated with the classic glamour of a bygone era and not the magazine-slick pages of a publication like Playboy. But the spread made sense, as Von Teese credits finding her father’s Playboys when she was a teenager as an influence on her lingerie-clad style.
Seventies sex symbol Farrah Fawcett consistently declined to pose nude during the height of her career. She waited until her late 40s and 50s to be photographed for Playboy. The 1997 issue, her second time posing, was released alongside a video called Playboy: Farrah Fawcett, All of Me . In it, the Charlie’s Angels star uses her body to paint a canvas.
Madonna didn’t pose for the magazine willingly. In 1985, during her first concert tour in North America (with the Beastie Boys opening), Penthouse and Playboy published nude photos of the singer taken during the 1970s. She tried to stop them from being published, to no avail — and then she took an unapologetic stance about the pictures, refusing to be shamed. Madonna addressed the photos during the Live Aid charity concert, criticizing the media.
In 1999, during the height of her career as a supermodel, Naomi Campbell wore a bikini and furs for her 14-page appearance in the magazine. Mixing nudity and professional modeling was still a daring thing to do at that time, but Campbell’s photos were just as artistic as those in her high-fashion portfolio. Fellow fashion icon Cindy Crawford also posed for the magazine.
During Drew’s Poison Ivy era, you know, the ’90s, the actress was breaking out of her childhood sweetheart persona, made famous in the movie E.T., and went wild. Her appearance in Playboy was part of the controversy all the teen rags were reporting at that time. Steven Spielberg, her former director and her godfather, sent the actress a quilt following the publication of her nude spread. The note attached read, “Cover yourself up.”
Charlize Theron appeared on the cover of Playboy for their 1999 issue, but the images in the magazine were captured before she became famous for her roles in films like Monster. The star sued, but the images went to press.
Twenty-one-year-old Brooke Shields posed for Playboy, though the controversy wasn’t quite the same as that time she posed nude for photographer Garry Gross (and Playboy Press) at only 10 years old (for a project called The Woman in the Child).
Apple-cheeked Sally Field posed for the magazine after establishing herself as an Academy Award-winning actress in movies like Norma Rae.
While this article is about Playboy, we have to mention a few men who posed for the company’s sister magazine, Playgirl (or were, at least, featured on the cover). We’ll leave these right here for you without comment.