1. Wesley Snipes

When it comes to owing money to the IRS, there is no one who is more outstanding and darker than Wesley Snipes.

On April 24, 2008, actor Wesley Snipes was sentenced to three years in prison for willful failure to file federal income tax returns.

Snipes, who owes the IRS $13,000,000 was recently ordered to start serving his prison sentence, but will try and plea for bail for the tax evasion sentence.

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