As the news hit the world that Playboy founder Hugh Hefner had passed away, people began reminiscing about the 91-year-old’s many Playboy magazine covers.
Originally pinned as a magazine for men, Playboy magazine was kickstarted in 1953 with a photo of Marilyn Monroe on the makeshift cover.
Over the years, Hefner used his beloved “Playmates” as cover models, as well as some of the world’s biggest celebrities, including Kim Kardashian, Charlize Theron, and Madonna.
Top models also graced the cover (Naomi Campbell and Kate Moss, to name a few), as well as unexpected cover models, such as Marge Simpson (yes, the cartoon) and Donald Trump.
Nude or fully clothed, here are the most iconic cover models in the magazine’s 64-year history.
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