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Playboy Sexy Centerfolds posing nude for Playboy Plus in sexy pictures set at Babes & Girls.Anderson was never far from the spotlight thanks to her many controversies (the sex tape with Tommy Lee) and six marriages to five men, but despite all this, she remained one of the most iconic Playmates of all time. 2. Jenny McCarthy. Jamie Lamor Thompson/Shutterstock. Playboy is an American lifestyle magazine made for men. Hugh Hefner founded it back in 1953. The first coverstar of the Playboy was actress Marilyn Monroe. She did an erotic photoshoot, but only non-nudes where published on December 1, 1953. Pamela Anderson is the Playmate with the most nude appearance by the way.Clockwise from top left: July 2019 Playmate Teela LaRoux, August 2019 Playmate Geena Rocero, September 2019 Playmate Sophie O'Neil, October 2019 Playmate Hilda Dias Pimentel, November 2019 Playmate Gillian Chan and December 2019 Playmate Jordy Murray. 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