18. Lauren Silverman
Before she had a baby with Simon Cowell – a man with a net worth of $43 million – Lauren Silverman was already married. In fact, she was hitched to none other than the music mogul’s closest buddy, millionaire Andrew. Ouch. But according to an interview Cowell granted Ellen Degeneres in 2013, Silverman is far from being just after his cash. Their union was rather “awkward” though.
17. Holly Madison
Holly Madison dated the much-older Hugh Hefner for a while, but once they were done she published a book about it. Hefner’s son Cooper was furious. “How does a person who is famous for being a gold digger paint themselves as a victim?” he wrote on Twitter in 2015.
16. Crystal Harris
Crystal Harris was the last in Hugh Hefner’s long line of blonde beauties. They had a rocky relationship – first time around, she called off their wedding with just five days until the big event – and no end of people calling her a gold-digger. That being said, she saw out his days with him right up to his passing this year.