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Donna Michelle, the 1964 Playmate of the Year, contorts herself into the Playboy bunny logo. Uncomfortable, probably, but impossible not to stare at. Playboy Enterprises 4/15 June 1965.

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15 Photos Hugh Hefner opened his first Playboy club in Chicago in 1960, starting a revolution for women who were legitimately proud to work there. Known as the ultimate gentlemen's retreat, key-holding patrons stalked the clubs as they were waited on by countless beautiful ladies.

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Goldie Hawn For the January 1985 issue , Goldie Hawn posed in a giant martini glass on the cover of Playboy. Photo : Ralph Dominguez/MediaPunch /IPX. Madonna Madonna looked like an absolute pop.

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