He also convinced her to change her name from Barbara Lynn Klein to Barbie Benton as it was more marketable.
Benton assumed a place beside Hefner, and the two were lovers for many years.
Jenny remembered Hef with a sweet photo on Wednesday.
Gradow has been faced with a number of setbacks; most notably, in 2006, he was charged to court for tax fraud and for altering interest rates and due dates for his gain.
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She landed the variety show of country music Hee Haw and continuous enjoyed her singing career.