The 27-year-old alleged golddigger thought her 90-year-old husband would leave her a hefty sum when he passed away in 1995 after their marriage of just over a year. But when oil mogul J. Howard Marshall II bequeathed $0 to Anna Nicole Smith, Smith’s bank account read the same amount. She sued his $1.6 billion estate for a cut, claiming that Marshall had expressed his intention to set up a trust for her and alleging sabotage by Marshall’s son Pierce, who received the lion’s share of the money. While the case was being fought, Smith was slapped with a judgment in a sexual harassment lawsuit by a former housekeeper. The judgment was based on perceived earnings from the estate, so Smith owed $850,000 in the case. She was forced to declare bankruptcy in 1996, while continuing to fight for her $400 million portion of the Marshall estate. But a series of legal flip-flops kept any money out of her hands, until her claim was finally rejected by the Supreme Court in 2011 – four years after her death.