51. KIM BASINGER We don’t mean this as a disservice to women like Kelly Brook and Nicolette Nightingale, but few Playboy cover girls ever make the transition from bare-skinned bombshell to Oscar-winning actress. That’s what makes Kim Basinger such an enigma: A leading lady with both the chest and chops to rule Hollywood. Basinger used her blonde locks and big lips to become a model in the 1970s, a movie icon in the ’80s, and an award-winner for her role as a prostitute in L.A. Confidential.