The 19 Hottest Celebs to Grace the Pages of Playboy

8. Madonna

It seems Playboy has a history for reviving old photos as the Madonna Playboy issue played out much like that of Charlize Theron. When she broke out as a singer and was about to start a film career in 1985, Playboy found some pictures they took before she was famous. Unlike Charlize though, Madonna did not fight against the magazine and the issue became iconic for both Madonna and Playboy.