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Description:Ines Rau Miss November    Playmate of the Year[ edit ] In the early days of Playboy, there was no official prize for the most popular Playmate at the end of each year. Dolores Donlon August is the oldest Playmate to date, appearing in her shoot at the age of Marilyn Monroe , who was featured in the first issue, was the only one to appear as "Sweetheart of the Month". The PMOY, Hope Dworaczyk , did appear on the cover, and was the first model to be the subject of a three-dimensional Playboy centerfold photograph.