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.
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.