Kimberly Conrad Then
Kimberly Conrad was was crowned Playmate of the Year in 1989 and, in the same year, became Hugh Hefner’s second wife. She gave birth to Hef’s two sons, one of whom is chief of global partnership for Playboy Enterprises. She and Hef split after nine years of marriage, divorcing 11 years after that. She lived next door to the Playboy Mansion while raising her sons.