7 – Pamela Anderson
With a beer t-shirt, Jumbo Tron and a Canadian Football League game to thank for the launch of her modeling career, Pamela Anderson was only 23 years old when she first appeared in Playboy.
Spending over 22 years gracing the magazine’s covers and feature stories, Anderson went on to star in Baywatch only to make even bigger headlines after very public relationships with notorious bad boys like Motley Crue drummer Tommy Lee, singer Kid Rock and poker player Rick Salomon.
While fans were long accustomed to Anderson’s ever-growing bust size, her appearance took a different turn in the early 2000s leaving many to assume she was using drugs.
Admitting in 2014 that she had been addicted to cocaine and alcohol, Anderson said she often did it to numb the tragic memories of her childhood. Finally entering rehab to get clean, Anderson’s sobriety seems to be going well after dumping many of her old friends and relationships that only enabled her wild habits.