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Carrie eventually dropped the litigation, but we wonder if she was still trying to get at Hefner when she launched "Playboy" competitor "Nude" magazine in 2008.Kimberly Conrad 1989 was a good year for Kimberly Conrad: the former Miss January 1988 was named Playmate of the Year AND she ended Hugh Hefner's 35-year bachelor spree by marrying the ultimate playboy.Sondra Theodore Sonda Theodore was a Sunday school teacher turned Playmate of the Month (July 1977).No wonder she liked Hef so much – he was the exact opposite of her data sheet turnoff: "People who don't live their lives to the fullest, who never reach for what's around the corner." She lived with Hef in the late '70s and was a member of the "Singing Playmates." But her real claim to fame is that she's one of the lovely ladies (the other is Patti Mc Guire) portrayed with Hef on the 1978 Playboy pinball machine.

Her new beau suggested she change her name to Barbi Benton, and a '70s pop-culture icon was born.They were together for nine years and had two sons (Marston and Cooper) before splitting.But they never divorced and remain married, living in separate side-by-side houses, to this day.Brande Broderick Hugh Hefner met actress Brande Broderick at L. hot spot the Opium Den, and she quickly became his number one – but not only – girlfriend.About a month later, at another local haunt called the Garden of Eden, Hef met twins Sandy and Mandy Bentley, who along with Brande (and later Jessica Paisley) became the Foursome.

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