7. Lindsay Lohan | Failure to Pay
As TMZ reported, in 2012, the IRS confiscated all of the starlet's bank accounts to cover the more than $230,000 she owed in unpaid taxes from 2009 and 2010. The seizure came after her "Scream 5" costar Charlie Sheen gave Lohan $100,000 to put toward the debt. In 2017, the IRS filed another lien against LiLo, then living abroad, alleging that she still owed more than $100,000 in taxes for income earned in 2010, 2014, and 2015, according to People.
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8. Chuck Berry | Filing False Returns
Three days after performing for then-president Jimmy Carter, the late "Inventor of Rock and Roll" received a sentence of four months in prison, four years of probation, and 1,000 hours of community service, according to The New York Times. The sentence followed a plea deal after an indictment for evading $109,000 in taxes and filing false returns. The IRS had spent five years investigating Berry, who famously insisted on being paid up front for every show in cash.
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9. Pete Rose | Failure to Report All Income
According to The New York Times, the all-time Major League Baseball hits leader spent five months in prison in 1990 for tax evasion for failing to report nearly $350,000 in income earned through the sale of memorabilia and autographs and appearances at card shows from 1984 to 1987.
His tax troubles didn't end there. In 2004, the IRS placed another lien on Rose, alleging that he owed nearly $1 million in back taxes for earnings from 1997 to 2002.
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10. Lil Wayne | Failure to Pay
"Weezy" settled a $7.7 million debt to the IRS in 2012 after the agency had threatened to seize the rapper's Miami mansion, according to the Daily Mail. The debt included $3.35 million owed in 2008, $2.25 million in 2009 and additional taxes and fees for unpaid taxes in additional years. In 2018, Lil Wayne told a crowd at a Chicago concert that fellow rapper Jay-Z helped him with the taxes, though it's unclear what type of assistance Hova provided.
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11. Joe Francis | Filing False Returns
The founder of the "Girls Gone Wild" adult entertainment franchise pleaded guilty in 2016 to two counts of filing false tax returns. As Fox News reported, in exchange for the guilty plea, Francis agreed to pay $250,000 and receive credit for 10 months he had already spent in jail in connection with the 2007 indictment. He admitted to failing to report more than $560,000 in interest income on his 2003 tax return.
Prosecutors had also claimed that Francis included more than $20 million worth of fraudulent business deductions on his taxes, a claim disputed by his attorneys.
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12. Darryl Strawberry | Failure to Report Income
In 1995, The Straw Man pleaded guilty to one count of tax evasion related to $344,00 in unreported cash earnings from autograph signing shows and personal appearances. He was back in hot water in 2007, when the IRS sued him to collect $500,000 in back taxes from four years between 1989 and 2004.
To cover the debt, Sports Illustrated explained, the agency seized Strawberry's deferred compensation from the Mets. An anonymous buyer purchased the annuity at auction for $1.3 million in 2015, receiving nearly $9,000 per month from the Mets for 18 years.
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13. Chris Tucker | Failure to Pay
The comedian and "Rush Hour" actor was in final discussions this year to settle an alleged tax debt worth $9 million, according to Radar Online. The debt reflects unpaid taxes from four years between 2002 and 2010, ranging from $470,000 to more than $4.5 million. Tucker has agreed to multiple payment plans with the IRS to chip away at the debt, and when he sold one of his homes in 2020, he used some of those proceeds to pay the IRS.
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14. Stephen Baldwin | Failure to Pay State Income Taxes
After pleading guilty to a felony charge that he failed to pay state income taxes from 2008 to 2010, the youngest Baldwin brother paid back a total of $400,000 in installments ending in 2014. According to CBS News, Baldwin did not have to spend any time in jail in connection with the charges. After court, the actor said that the tax challenges had been a "great learning curve" and that he planned to "reconstruct my personal finances and do the right thing."
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15. Teresa Giudice | Concealing Income
According to The Sun, the Real Housewife of New Jersey owes more than $1 million in federal and New Jersey state taxes. That includes liens for various amounts of allegedly unpaid taxes from 2000 through 2021.
According to theU.S. Attorney's Office, District of New Jersey, "the Giudices intentionally concealed businesses they owned, income they received from a rental property, and Teresa Giudice's true income from the television show 'The Real Housewives of New Jersey,' website sales, and personal and magazine appearances." In 2022, she paid off more than $360,000 in liens related to 2011 and 2012 taxes.
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16. Mike “The Situation” Sorrentino | Falsifying Income
The "Jersey Shore" star pleaded guilty in 2008 to one charge of tax evasion, in connection to 2014 and 2017 indictments that alleged he did not pay taxes on nearly $9 million in income. People reported that Sorrentino's guilty plea got him an eight-month prison sentence, which he served in 2019, a few months after getting married. Upon release from prison, Sorrentino and his wife put out a statement saying that they were "elated to finally close this chapter of our life."
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17. Richard Hatch | Failure to Pay
Even after spending more than four years in prison on charges of tax evasion, the winner of the first-ever season of "Survivor" maintained that he was innocent of the claims. "I never did anything deserving of prison time," he told Oprah years later, according to Yahoo. "I never attempted to evade taxes, which was what I was convicted of." Hatch's conviction in 2006 stemmed from charges that he did not report $1.43 million in income received from winning "Survivor" in 2000.
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