German authorities accused tennis legend Steffi Graf of tax evasion in 1995. Further investigation revealed the tax cheat was actually Steffi’s father, then manager of Steffi’s finances. The charge against Steffi was dropped (she paid back what she owed, 1.3 million deutsche marks), while her father, Peter Graf, ended up spending 25 months in prison.

In 2008, Annie Leibovitz borrowed $15.5 million from a financial company in order to pay federal and state tax liens totaling more than $1.4 million, and also to make mortgage payments on multiple homes and settle large debts with vendors. A significant part of the collateral Leibovitz presented in exchange for the loan was the copyright to virtually every single one of her photographs.

Sometimes known as the Hollywood Madame, Heidi Fleiss got busted in the early 1990s for operating a prostitution ring that catered to the entertainment industry. Convicted of income tax evasion and related crimes, she served 21 months of a three-year sentence in a federal penitentiary.

Leona Helmsley, or the Queen of Mean as the press dubbed her, was famously alleged to have said, "We don’t pay taxes. Only little people pay taxes." In 1989, the late billionaire hotel operator was convicted of federal income tax evasion among a litany of other tax crimes. She was sentenced to 16 years in prison, but spent only 19 months behind bars.

Janine Lindemulder is the porn star ex-wife of Jesse James, the celebrity motorcycle builder. Lindemulder pled guilty in 2008 to charges of willful failure to pay federal income taxes. She was sentenced to six months in prison and ordered to pay $200, 000 in back taxes plus fines. Upon her release in 2009, she entered into a custody battle with James over their daughter. Sandra Bullock, James’s ex-wife, contributed testimony. In December of 2009, roughly one year after Lindemulder pled guilty in a federal court, James won the custody case. FOR A SUCCESS STORY ON WOMEN WHO HAVE FALLEN INTO MONEY, READ "MONEY CHANGES EVERYTHING: FINANCIAL WINDFALLS" HERE.