Six months before she appeared in a Playboy centerfold, Anna Nicole Smith (then known as Vickie Smith) met oil tycoon J. Howard Marshall while she was dancing at the Houston gentlemen's club, Gigi's. Over a two-year courtship he lavished gifts on the busty blonde model until the two were married. When Marshall died in 1995 after thirteen months of marriage, Smith battled Marshall's son E. Pierce (technically her stepson, who was 28 years her senior) in court for the $1.6 billion estate. She initially won close to $500 million, which a federal judge later reduced to $88 million. Smith died of a drug overdose in 2007.