DMX was sentenced to a year in prison for tax fraud on March 29, 2018. The U.S. Attorney's Office for the Southern District of New York filed charges against the rapper in July 2017. According to the office, DMX, whose real name is Earl Simmons, hid millions of dollars in income over multiple years to avoid paying $1.7 million in taxes.
In April 2012, the IRS filed a $1.7 million tax lien against skier Lindsey Vonn and her then-husband, manager and coach Thomas Vonn. The two were separated at the time. Vonn said in a statement that "not being in control" of her finances was the problem.
"The money owed was for the 2010 tax year, which was filed on time, and it has been paid in full," Vonn said in a statement on her Facebook page at the time. "This is an important lesson for me. Not being in control of my finances and relying on someone else who you believed had your best interest at heart was a mistake and one I will not make twice."
Home and garden businesswoman Martha Stewart was sentenced to five months in prison plus five months of home confinement in July 2004. Stewart did time for insider training, but had to pay $220,000 in back taxes to the state of New York for her property in the state before going to prison.
In 2008, actor Wesley Snipes served a three-year prison sentence when he was convicted of three misdemeanor counts of failing to file tax returns from 1999 to 2001. The "Blade" trilogy star avoided paying $7 million in taxes at that time. He entered McKean Federal Correctional Institution on Dec. 9, 2010. In July 2010, a federal appeals court denied Snipe's claim that his three-year sentence was unreasonable. He was released in April 2013.
Country legend Willie Nelson got creative when it came time to pay off his IRS debt. In 1990, the federal agency placed liens on Nelson's property for a total of $16.7 million. His lawyer negotiated the debt to $6 million by his lawyer, but Nelson couldn't pay it off. The feds took nearly everything from Nelson's home and auctioned most of the property to pay the debt, and a portion of the debt was paid with the 1991 album, "The IRS Tapes: Who'll Buy My Memories?"
Singer and rapper Lauryn Hill served a three-month prison sentence in Connecticut in July 2013 after she failed to pay more than $1 million in taxes. Hill pleaded guilty in 2012 to tax evasion on $1.8 million between 2005 and 2007. At the time, she told the judge she had always meant to pay the money, but her hiatus from music meant she couldn't pay her taxes. Her attorney said in May 2013 that Hill had paid $970,000 to satisfy her penalties and unpaid bills before entering the minimum security prison.
Reports emerged in 2016 of more tax trouble, but Hill said it was a continuation of her previous tax issues.
The IRS filed a $6.2 million tax lien on Nicolas Cage in July 2009 and a $6.7 million tax lien on the star in December of that same year. Before then, the quirky actor reportedly bought two castles, an island, a dinosaur skull, shrunken pygmy heads and more than a dozen mansions. Cage paid off the $6.2 million in 2012 and continues to take film roles to pay off his debts.