Anna Nicole Smith (Bankrupt in 1996): A sexy Playboy playmate in her late 20s, Anna Nicole sidled up to the elderly but filthy rich J. Howard Marshall, who made a fortune of $1.6 billion in the oil industry. They were wed and after 14 months, Marshall died. Smith expected to inherit a bundle … but the courts decided she would get nothing. The result of a $400 million budget going to zero was mighty painful, and resulted in bankruptcy. Adding to the troubles was that a former female maid sued her for sexual harassment and the resulting $850,000 fine was tacked on. Anna Nicole led a troubled life after that, including drug abuse and death under odd circumstances in 2006.
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