Cornell Iral Haynes Jr. (AKA rapper Nelly) owes the IRS more that $2.4 million. Though his fans try to get him out of debt by streaming his songs online, the IRS is considering another option: use the ticket sales he collects from his latest tour to pay off the debt.
Actor Dustin Diamond of "Saved by the Bell" fame owes Wisconsin $93,768 in back taxes.
Ron Mix, a Pro Football Hall of Fame member, is facing up to three years in prison after pleading guilty to a Missouri tax fraud charge. He agreed to pay the IRS about $50,000 for one count of making false statements on a tax return. The statements are related to illegal payments he submitted as a San Diego lawyer to a non-lawyer for client referrals. Mix donated about $155,000 over a three-year period to a charity the non-lawyer operated, and Mix reported the payments as charitable deductions.
Singer-rapper Trey Songz received a tax lien from the IRS on October 8, 2015 over taxes he did not pay for his 2013 income. He paid $750,000 to the IRS on October 28 to cover his $748,870.08 debt.
In 2014, the IRS filed a $369,249 tax lien against singer-actress Vanessa Williams for unpaid 2011 taxes.
Busta Rhymes, a rapper who rose to fame in the mid-90's, is facing two tax liens from the Department of Treasury: $611,000 for 2008 and $178,000 for 2012. Altogether, he owes the IRS nearly $800,000 in unpaid taxes.
In 2008, former businessman William Berroyer was settling a repayment deal with the IRS for his $60,000 tax bill when he tripped and fell over a telephone cord in a Hauppauge, NY IRS office. He spent 17 days in hospitals and rehab clinics for his injuries, and sued the IRS for $10 million (claiming that the injuries prevented him from enjoying his favorite activities). A judge ruled in favor of Berroyer in 2014, but reduced his payment to $862,000. In addition, Berroyer's tax bill was waived.
H. Ty Warner, creator of the famous 90s plush toy Beanie Babies, pled guilty in January 2014 to tax evasion of $25 million using Swiss bank accounts, but was able to avoid a prison sentence. Warner was given leniency by the judge for his philanthropic activity and charity donations. He will instead serve two years’ probation and perform 500 hours of community service. Warner also agreed to pay $27 million in back taxes and interest, as well as a civil penalty of more than $53 million.
Lauryn Hill, a 90’s Grammy-winning singer, was convicted in May 2013 of failing to pay nearly $1 million in taxes. She served her sentence and was released on October 2013 from her three-month sentence at a federal prison in Connecticut. The singer was allegedly unable pay her taxes due to during a period of time when she was inactive as a musician.
In 2013, the Pennsylvania Department of Revenue filed a $39,000 tax lien against former reality TV star Jon Gosselin for taxes he did not pay in 2009.
Legendary R&B singer Dionne Warwick filed for bankruptcy in 2013 after she battled the IRS for years over $10 million worth in tax debt dating back to 1991.
Former NFL player O.J. Simpson has found himself in hot water numerous times. He was accused of murder, acquitted, but then found liable in a civil suit. In 2008 he was sentenced to 33 years in prison for the robbery and kidnapping of a sports memorabilia salesman. Now he is guilty of tax evasion. According to the IRS, he hasn't paid any taxes since 2007, and reportedly owes almost $180,000. A second lien was filed early in 2013, covering $17,015.99 in income taxes for 2011.
The IRS has filed two tax liens on comedian Katt Williams: one in 2012 for failing to pay $3.2 million for 2008 and $829,352 for 2009, and another in 2010 for failing to pay $284,000.
In 2012, the IRS filed a tax lien on legendary singer/songwriter Lionel Richie for $1.1 million in unpaid taxes from 2010.
In 2012, Krystle Marie Reyes fraudulently filed an Oregon state tax return that reported $3 million in earnings and managed to receive $2.1 million in tax refunds through state-issued refund debit cards. She then proceeded to go on a shopping spree, spending her fraudulently obtained refund money at a rate of tens of thousands of dollars per week. This case is considered to be one of the largest instances of tax fraud in the history of Oregon.
Plaxico Burress, a Super Bowl champion wide receiver, had a federal tax lien filed against him in 2012. The IRS said he and his wife did not pay income taxes in 2007 and 2009, leaving an outstanding bill of $98,064.76. He was also the target of a New York State lien, alleging he owed $59,241 in unpaid income tax for 2007.
Stephen Baldwin, who made his name in movies and reality TV, was arrested in December 2012 and charged with failing to pay more than $350,000 in New York state income taxes. In addition, he reportedly did not file tax returns for 2008, 2009, and 2010. By pleading guilty to one count of repeated failure to file and paying $100,000 to New York in restitution, he avoided prison time. He submitted his final payment of $100,000 in April 2014.
The IRS seized actress Lindsay Lohan's bank accounts due to her unpaid tax debt. Fortunately, the IRS released her from a tax lien in 2012 when she was able to pay off her 2009 using a $100,000 check actor Charlie Sheen gave to her. However, debts from 2010 and 2011 remain, but her business manager reportedly said he is working on a settlement to pay off the six figure balance.
Rapper Lil Wayne has three separate tax liens against him: $1.13 million in December 2010 for tax years 2004, 2005, and 2007; $5.6 million in 2011 for tax years 2008 and 2009; and $7.72 million, which he paid at the end of 2012. He currently has a $12,155,084.46 tax bill.
Popular R&B singer R. Kelly gained his fame in the 90’s and early 2000’s and sold an estimated 50 million records worldwide, earning him a great fortune. However, he failed to pay his taxes between the years 2005 and 2010 and reportedly owes $4.8 million for that time period. In addition, he owes nearly $1.4 million for 2011.
American skier Lindsey Vonn and her estranged husband reportedly owed $1,705,437 in back taxes from 2010, the year she won the gold medal during the Vancouver winter Olympics.
Kevin Federline, the ex-husband of famous pop star Britney Spears, faces $57,615 tax lien filed by the IRS for unpaid taxes in 2009 and 2010.
In 2009, professional race car driver Hélio Castroneves was charged with filing years of false tax returns and evading $80 million in income taxes. His defense attorney does not deny the charges, but says that the racer is not to blame due to a brain injury which had compromised his decision-making abilities.
In 2009, Floyd Mayweather Jr. , a successful boxer with a history of tax problems, was given a $5.6 million bill by the IRS for unpaid taxes. He has agreed to pay them since then.
Bronx-born rapper Fat Joe (Joseph Cartagena) faces up to two years in prison, as well as a fine of $200,000 plus IRS penalties and court costs, after pleading guilty to failing to file tax returns in 2007 and 2008, when he made almost $3 million.
Actor Nicolas Cage failed to pay $6.2 million in taxes on the $24 million he earned in 2007. He claimed that his accountant made mistakes. In the end, he had to sell several of his houses to obtain the money to pay back the IRS.
Ja Rule (Jeffrey Atkins), amoderately successful rapper and actor, was charged with 3 counts of tax evasion for neglecting to pay his taxes from 2004 to 2006. He served 28 months in prison.
Allegedly, Flavor Flav (William Jonathan Drayton, Jr.), frontman of hip hop group Public Enemy, owes $906,250.56 in back taxes from 2004-2006.
Wesley Snipes, an actor who starred in several movies in the 90's and early 2000's, failed to pay taxes from 1999 to 2004. He tried to make the claim that he was a resident alien of the United States (he failed to realize that they have to pay taxes too). Naturally, because he was born in Florida, the IRS didn’t accept his claim and he was sentenced to 3 years in prison. He managed to get out on bail, but he owes the IRS $17 million in taxes.
Pete Rose, a famous baseball player, was accused of betting on baseball games, which he adamantly denied, but was later found guilty. In addition, the IRS accused him of not reporting income from special appearances and autographs, which led to a $50,000 fine and 1,000 hours of community service. In 2003, he was found guilty of not paying taxes again, and had to pay $154,000 and sell his condo in Los Angeles.
Famous bounty hunter and reality TV star Duane “Dog” Chapman reportedly owes the IRS $2 million in unpaid taxes dating back to 2002.
Daytime TV host and home guru Martha Stewart failed to pay $220,000 worth of taxes on an estate she owned, claiming that she wasn’t there enough, so she shouldn’t pay them. The IRS disagreed and forced her to pay the amount in 2002.
Actor and comedian Chris Tucker reportedly owes the IRS over $14 million in unpaid taxes, dating back to 2001.