24. Trey Songz
> Debt: $250,000
The Grammy-nominated artist, whose real name is Tremaine Aldon Neverson, has had R&B/hip-hop hits that included “Say Aah,” and “Bottoms Up.” He got slammed with a federal tax lien in 2015 on his income from 2013.
23. Pete Rose
> Debt: $366,000
Baseball’s all-time hits leader, who’s banned from baseball for life for betting on the national pastime, ran afoul with the IRS for failing to report income from autograph and memorabilia sales and personal appearances starting in 1984. Rose served a five-month stint in federal prison for tax evasion. He was hit with tax liens in 2004 and 2012.
22. Val Kilmer
> Debt: $498,000
The “Batman Forever” and “Top Gun” star had no sooner satisfied a $538,000 debt to the IRS in 2010 than the government hit him with a lien against his $18.5 million New Mexico ranch for unpaid 2008 taxes of $498,165.
21. Christie Brinkley
> Debt: $532,000
In 2011, the IRS placed a lien on the $30 million Hamptons estate of this supermodel and actress – and former wife of Billy Joel – charging her with a debt of $531,720 for back taxes. She paid off the amount owed the same year.
20. MC Hammer
> Debt: $780,000
The taxman came after MC Hammer, the “U Can’t Touch This” rapper, for back taxes on his earnings in 1996 and 1997, seeking a total of $779,585. Hammer, born Stanley Burrell, was known for his large entourages, and they cost him so much money to maintain per month, that he filed a bankruptcy claim in 1996 listing $13 million in debts.
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