Isley Brothers singer Ron Isley was sentenced to three years in prison in 2006 for $3 million he owed the IRS. In September 2006 a court found him guilty on five counts of tax evasion and one count of willful failure to file a tax return. He was released April 2010 at 68.
Jerry Lee Lewis
Lewis had $560,000 worth of tax debt in 1984. Cutting a deal with the government, Lewis set up a 900 phone number charging callers $2.75 a minute to hear random stories about his life, including a story about his first date and a childhood fight with a schoolteacher.
36-year-old Ja Rule (real name: Jeffery Atkins) was released from prison on Feb. 11 after serving 20 months on a gun possession charge. But he immediately entered another jail for tax evasion. In July 2011 the U.S. Attorney's Office in New Jersey found that the rapper owed $1.1 million in taxes stemming from royalties and tour profits and he plead guilty to three counts of failing to file tax returns from 2004 to 2008.
Mary J. Blige
The singer, 42, recently was hit with a $901,769.65 tax lien in the State of New Jersey. No word yet on how payment is coming along.
Infamous for tax troubles, Toni Braxton’s woes with Uncle Sam remain at epic proportions. The one-time hit-making R&B vocalist filed for bankruptcy due to a nearly $4 million debt in 1998. She’d later file bankruptcy again in 2010 after defaulting on a $900,000 loan to City National Bank and owing several other companies.
The IRS charged Lil’ Kim (real name: Kimberly Jones) with nearly $1 million in back taxes in 2005. At her trial Kim surprised the judge with the fact that she worked for tax preparers H&R Block prior to her rap stardom.
In 1968 the IRS informed Brown that he owed nearly $2 million and eventually added $4.5 million to the tab. Already Soul Brother No. 1 and owner of several radio stations, homes, cars, and even a plane, the government snatched a chunk of his property to settle debts. His troubles continued throughout his career.
In 1979 the rock 'n' roll legend was sentenced to four months in jail and 1000 hours of community service when the IRS found Chuck Berry of evading $200,000 in taxes. Coincidentally, that was the same year President Jimmy Carter invited the star to play at the White House.
Last summer eight-time Grammy-winning singer Lauryn Hill plead guilty to not paying federal taxes on more than $1.5 million earned over three years -- from 2005 to 2007.