17: Janice Dickinson

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Janice Dickinson is the world’s first supermodel as well as a former judge on America’s Subsequent Top Model. She is 60 plus now and has spent more of her later years doing plastic surgeries. Seems to be funny, right! And to make things worse she’s had her share of legal beating.

She owed $550,000 in back taxes and mortgage loans, $8,000 to Beverly Hills dermatologist, $300,000 to City National Bank and tens of thousands in medical bills. However, she found an easy way out of her troubles. Her fiancé, Dr. Robert Gerner aided her to pay off a small portion of her Mortgage Loans.