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Arguably the most famous (if not the only) lifestyle guru-turned-jailbird, Stewart served five months in federal prison for lying to investigators about an insider trading deal. But before getting locked up in 2004, the celebrity was ordered to pay $220,000 in back taxes on her New York mansion.
When it came to explaining why the Blade star didn't pay taxes on more than $58 million in income, Snipes tried every excuse in the playbook. The jury didn't buy the actor's claims that he was exempt from paying taxes because he was a nonresident alien, or that his advisers had led him astray, and Snipes served less than two years in prison for the crime.
The winner of Survivor's first season made quite the costly mistake when he didn't pay taxes on his $1 million bounty, claiming CBS agreed to foot the bill. In the end, Hatch was sentenced to prison on two different occasions in 2006 and 2011.
In July 2013, the Real Housewives of New Jersey couple were charged with conspiring to defraud lenders and illegally obtain mortgages and other loans, as well as hiding assets and income during a bankruptcy case. The 39-count indictment claimed they were responsible for mail and wire fraud, bank fraud, making false statements on loan applications and bankruptcy fraud. Teresa was sentenced to 15 months in federal prison while Joe earned a 41-month conviction.
The Dance Moms TV reality star is currently awaiting her October 11 sentencing date after pleading guilty to concealing bankruptcy assets and not reporting an international monetary transaction. Miller could have faced up to a $5 million fine and five years imprisonment on the initial bankruptcy fraud charges from her 2015 indictment, but per Deadline, her attorneys have been working with the court to strike a plea deal.
Though she's never faced criminal allegations, the pop sensation's financial situation raised eyebrows when it was revealed she dropped almost $38,000 on pet care for her dogs and a whopping $68,000 on pampering, including massages and mani/pedis in 2015.
The Fugees songstress checked into prison for three months in 2013 after failing to pay close to $1 million in taxes over the last decade. Hill pleaded guilty to the charges, telling the judge she had always intended to pay the money back.
The actor avoided jail time for failing to pay $350,000 in taxes between 2008-2010. Baldwin's older brother Alec spoke on the issue in 2012, telling Piers Morgan Tonight, Stephen was "no different than millions of other people," in that he spent money he had that should have been put aside to pay taxes.
The country music singer's financial troubles are well known, as his $16.7 million tax bill (later negotiated to $6 million) was one of the largest ever issued at the time. But after he failed to pay back the amount, and in 1990 officials raided his home and took all of his belongings with them.
The former Baywatch babe was in the red for more than $493,000 in personal income taxes in 2010.
The Grease alum acknowledged he short-changed the government and agreed to pay $607,400 in back taxes in 2000, about half the $1.1 million in back taxes and penalties the IRS had claimed Travolta owed between 1993-1995.
Kurt Cobain's controversial widow admitted to losing $27 million in the aftermath of various lawsuits and other legal issues, and in 2014 the IRS hit the star with a $320,000 tax lien.
The Girls Gone Wild founder pleaded not guilty in 2008 to two felony tax-evasion charges after being accused of unlawfully deducting more than $20 million in bogus business expenses on multiple corporate tax returns.
The Internal Revenue Service filed a federal tax lien against LiLo in 2012 after the actress failed to pay not only her 2009 taxes, but those on her 2010 earnings as well, totaling around $140,203.30.
Financial woes seem to follow the R&B singer, as Braxton filed for bankruptcy in 1998 with nearly $4 million in debt. History repeated itself in 2010 when she filed bankruptcy once again after defaulting on a $900,000 loan.
In 2011, the heavy metal rocker and his wife were forced to pay Uncle Sam $1.7 million in tax debts.
The Olympic skier's money problems snowballed out of control in when the IRS demanded she owed $1.7 million in taxes from 2010.
He's won 5 Latin Grammy Awards, but his success in the music industry was overshadowed not once, but twice, when he paid the feds $2.5 million in 2007 for tax evasion and was slammed again three years later with a $3.4 million lien.
The actor lost a chunk of his National Treasure when he plunked down $6.25 million in 2012 to help pay off the massive back taxes he owed the IRS, but he still owes somewhere around $7 million. Yikes!