4. Anna Nicole Smith
There have been few Playmates who have lived such a controversial life in the public eye as 1993 cover star, Anna Nicole Smith. Her infamy exploded not long after her first Playboy appearance, when she announced that she was due to wed Texan oil billionaire J Howard Marshall, six decades her senior. His death (ten months into the marriage) resulted in a long and unseemly court battle as to whom would be entitled to inherit his $1.8 billion fortune. Arguably the seediest element of Smith’s life concerned the months leading up to her death of a prescription drugs overdose and the parentage of her daughter, Dannielynne. Though her new husband, Howard K Stern claimed parentage, up to five other men were realistically in the frame to be the father. A DNA test ultimately proved that photographer Larry Birkhead was Dannielynne’s biological father, a messy end to the sad story of Anna Nicole Smith.
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