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1. Martha Stewart: Stewart was forced to pay $220,000 in back taxes and penalties to the State of New York.

2. Ja Rule: Multi-platinum selling rap artist Ja Rule failed to pay taxes on more than $3 million that he earned between 2004 and 2006 while living in Saddle River, NJ.  He pleaded guilty to three counts of unfiled taxes, admitting he hadn’t filed for five years, according to U.S. Attorney Paul Fishman. The rapper was sentenced to two years in prison. The hip hop star told a federal judge that he had received bad financial advice and had trouble coping with fame.

3. Lauryn Hill: Next up is hip hop icon Lauryn Hill who just happens to reside in the Garden State of New Jersey. In 2012 the grammy-winning singer pleaded guilty in federal court, to three counts of failing to file federal income tax returns. Hill pleaded guilty to failing to file federal returns between 2005 and 2007, despite earning an income of more than $1.8 million. Each count carries a maximum penalty of one year in prison and a $100,000 fine.

4. Willie Nelson: After seizing most of his assets in 1990, the federal government forced Willie to pay over $16 million in back taxes and fines for his involvement with a bogus tax shelter.

5. Nicolas Cage: According to the IRS, in 2009 Cage owed approximately $6 million in back taxes. The actor accused his ex-manager and accountant of making poor investment choices.

6. Marc Anthony: In 2007, the IRS served Anthony with $2.5 million in back tax bills. Then in 2010, he received two additional bills totaling over $3 million for unpaid taxes on real estate. Marc Anthony also blamed management.

7. Heidi Fleiss: Known as “The Hollywood Madam,” Fleiss ran a prostitution ring during the early 1990s. Although she never named names, her business attracted clients who were well-known and well-off. Ultimately, she was arrested in June 1993. Fleiss was convicted of federal tax evasion charges, which carried a seven-year prison sentence.

8. Pete Rose: Rose made his name with the Cincinnati Reds, first as a player and later as a manager. Despite his many on-field accomplishments the Baseball icon was caught gambling on games, including those played by his own team. He was sentenced to five months in prison and fined $50,000 for tax evasion, according to The Associated Press.

9. Martha Stewart: The savvy business woman accumulated a $220,000 tax debt for not paying taxes on her East Hampton, New York, home, which she claimed she spent very little time at and therefore thought she didn’t need to pay taxes on. She was sentenced to five months in prison and five months of home confinement. Stewart was also fined $30,000.

Death and taxes may be equally inevitable, but Uncle Sam demands the last word.

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