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Denise Truscello/WireImage.com
A former Playboy Playmate, Anna Nicole Smith became famous when she married the uber-wealthy J. Howard Marshall, who was decades older. After his death, she was involved in a length battle over his estate, and later on entertained audiences with her reality series, The Anna Nicole Show. After the death of her son Daniel, Anna died of a prescription drug overdose in 2007, leaving behind her daughter, Dannielynn.