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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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New York Bunny Helena Antonaccio. *Courtesy of *Playboy. Benton, Hefner, and Bunnies disembark from The Big Bunny, Hefner's private DC-9, in New York, circa 1970. Photograph by Sam.


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1. Drew Barrymore - January, 1995 Nobody has ever used Playboy more perfectly than this. During a stretch of her career that sported titles such as THE AMY FISHER STORY, DOPPELGANGER, and WAXWORK.


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Sondra Theodore Sondra Theodore is a former Playboy Playmate who was named Playmate of the Month in the July 1977 issue; she's also one of Hugh Hefner's ex-girlfriends, and one of the women.


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25 Slides Courtesy of Playboy In honor of Hefner, we're taking a look back at Playboy Bunnies, and their iconic outfits. Advertisement - Continue Reading Below 1 December 1953 Courtesy.