Lauryn Hill was one of the most promising singers of the late ’90s. As part of the Fugees, she sang on a smash hit cover of Roberta Flack’s “Killing Me Softly With His Song,” and then in 1998 released her solo debut The Miseducation of Lauryn Hill. Hill wrote and produced most of the album, which sold 19 million copies and won five Grammys, including Best New Artist and Album of the Year.
It looked like Hill would be one of the biggest pop stars of the new millennium…but then almost nothing happened. The only album she’s released since was a live performance in 2002, which was marked by emotional breakdowns and bizarre stage banter. After that she retired from music to raise her five children.
But Hill is in the news again, and it looks like she’ll finally be releasing a follow-up to Miseducation…whether she wants to or not. Late last year, Hill pled guilty to charges that she failed to pay income tax on $1.8 million in royalties earned between 2005 and 2007. She made a $50,000 payment but still owes the federal government more than $500,000. This week, a judge gave her until May 6 to pay off the amount. Where will she get the money? From a brand-new deal with Sony Records—$1 million to record five new songs, and even more if she records a full album.
Will Hill finish the album and/or pay off her bills in time to avoid jail? Not quite. In spite of the deal, and even releasing a song, a judge still sentenced her to three months in prison. Here are some other musicians who forgot to pay their taxes, and their creative solutions.
• Willie Nelson racked up a $16 million unpaid tax bill by 1990. In 1992, he made a $3.6 million dent with the proceeds from his album The IRS Tapes: Who’ll Buy My Memories? He’s since paid off the rest.
• Jerry Lee Lewis eliminated $500,000 of tax debt in 1984 by charging fans $2.75 a minute via a 1-900 number to listen to Lewis tell anecdotes about his childhood.
• In 1979, Chuck Berry was found to owe the IRS $200,000. He served four months in jail and performed 1,000 hours of community service.