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Hugh Hefner, Barbara Benton

6th September 1969: American pornograpic magazine publisher and club owner Hugh Hefner with American actress Barbara Benton in a car, leaving London's Hilton Hotel for London airport. (Photo by Keystone/Getty Images)

Hugh Hefner's Many Exes

Before Playboy mogul Hugh Hefner takes a trip to the altar to marry on-again, off-again girlfriend Crystal Harris, take a trip down memory lane with omg! as we look back at some of Hef's gal pals from over the years.

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