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Chicago-born R&B superstar R. Kelly owes the Internal Revenue Service nearly $5 million in unpaid taxes dating as far back as 2005, according to tax liens filed recently in Cook County, the latest sign the Grammy winner’s finances are in disarray.

In April, the IRS filed liens against Kelly, claiming he owes a total of $4.8 million from six different tax years, including $1.4 million from 2005 alone. The filings do not mark the first time Kelly has drawn scrutiny from the IRS. Since 2008, he has paid more than $3 million in back taxes after the IRS filed liens against him, county records show.

The earliest tax lien on record against Kelly was filed for his 2006 bill, which would have been due as Kelly was in embroiled in a legal battle over child pornography charges. He was acquitted in 2008, the year the IRS said he failed to pay $1.12 million he owed.

Kelly’s representatives did not return a call seeking comment.

Kelly’s 22,000-square-foot mansion in south suburban Olympia Fields went into foreclosure last year, with JPMorgan Chase claiming that the singer, whose name is Robert S. Kelly, owed it $2.9 million. The house was listed for sale for about $1.5 million but has been pulled off the market.

Wilmette-based tax attorney Steven Blanc, a former IRS trial attorney who also has worked for a Hollywood law firm, said even millionaires find themselves coming up short at tax time — especially entertainers.

“They have managers, who are supposed to be watching their money,” he said. “But when you get a call from your client at midnight and they’re at a dealership and they ask you: ‘Is it OK for me to buy a Lamborghini?’ (the manager) always says yes, even if there’s no money in the checking account. Because if they don’t say yes, they get fired.”

The IRS liens will tank Kelly’s credit, but federal agents won’t be seizing his property anytime soon.

“This is something they do to get your attention,” Blanc said.

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