Trouble With Uncle Sam: Rappers Who Didn't Pay Their Taxes and Paid Dearly for It

It’s tax season! It’s pretty safe to say that no one likes taxes, but not paying them can have catastrophic consequences. When it comes to paying Uncle Sam, there is no escaping. You'd be surprised to learn about high-profile rappers who earned millions of dollars but failed to pay their taxes.

Thankfully, most of them settled their debts with the IRS and avoided jail time — but some have not been as lucky. Keep reading for a list of rappers who didn't pay their taxes and paid dearly for it.

Lil Kim has always been "All About the Benjamins," but according to TMZ, the rapper owed over $1 million in taxes.

The rapper accumulated an unpaid bill for every year between 2002 and 2009 — $1,026,862.42 to be exact.

In 2012, a representative for Lil Kim responded to TMZ's findings, stating that she "hired professional attorneys to handle this matter."

The rep added that her team of legal experts was working with the IRS to "amicably resolve the situation."

The owed taxes, in addition to the $2 million loan on her NJ home and $186,000 in unpaid legal bills, pressured Lil Kim to look for a legal way out. Her financial woes led her to file for bankruptcy in 2018.

As of 2023, Lil Kim has settled $1.4 million of her tax debt and is no longer considered to have unpaid taxes according to court documents obtained by RadarOnline.

In the past, Lauryn Hill noticeably went ghost from the music industry and her obligations to the IRS.

The Internal Revenue Service filed charges against Hill for failing to pay taxes on more than $1.5 million, earned from 2005-2007.

Hill went to her Tumblr account to explain her disappearance and the reason she did not file taxes: “When I was working consistently without being affected by the interferences mentioned above, I filed and paid my taxes.”

“This only stopped when it was necessary to withdraw from society in order to guarantee the safety and well-being of myself and my family," she explained.

After pleading guilty and paying about $970,000 in back taxes and penalties she was sentenced to 3 months in federal prison and three months in home confinement in 2018.

Many — including NBC News — questioned if the mother of six was singled out amongst tax invaders by having to serve prison time despite the fact she did not lie or falsify documents like other offenders.

Back in 2012, Beanie Siegel was sentenced to two years in federal prison for tax evasion. The rapper owed $728,536 to the IRS after failing to file returns between 1999 to 2005 — except for the time he paid $10,000 in 2001.

Despite earning over $1 million over the period between 2003-2005, he failed to play $358,077 in federal taxes (according to NBC Philidelphia.)

He reportedly earned more than $3 million from 1999-2005. However, Beanie said his earnings didn't match up with his financial responsibilities.

Beanie told "RapFix Live": "The State Property line, I only owned 20 percent of that. It was my idea, I brought that to the table."

"I brought the movie scripts which led up to all those movies [with] us that played in it — people don't know we only got SAG wages. We ain't get no money from that."

The rapper expressed that he thinks that taxes should be illegal and explained that the three years he was incarcerated prior prevented him from being able to take care of his business.