Annie Liebovitz

World famous photographer Annie Leibovitz might get paid loads, but she also racked up $715,000 in debt and owed money for unpaid taxes, a book project that fell through, equipment rentals and renovations on her town house. In 2008, Leibovitz also borrowed $15.5 million from Art Capital Group to cover her debts, putting the rights to her photos and her two homes up as collateral. You'd think she could probably earn that much in a couple years though, maybe? [ABC News]