In 2009, the former teenybopper was slapped with an IRS lien worth more than $1 million. They date back to 2003, leading Carter's current manager to make the statement, "It is unfortunate that while Aaron was a minor, his finances were grossly mismanaged by his previous team." Child stars...they just can't catch a break, can they?
With so many digits you'll have to squint to get the full number, Lil Wayne was hit with a tax bill of $12,155,084.46 in March 2014. It's not the first time the "Lollipop" MC dealt with the taxman: In 2012, he paid off the IRS with a check for $7.7 million to clear a similar charge for past unpaid taxes.
And for those counting: Both sums are more than most of us will ever make in our lives.
"It was a disaster," she told NBC. "And a lot of it came from not paying attention; a lot of it came from just trusting the wrong people. And it was a wakeup call, it was a huge humongous wakeup call for me to say 'Look, you don’t need any of these people around and I’m going to make sure that you see how fast they run when this happens.' And it was just the biggest wakeup call ever."
In 2011, the Black Sabbath singer, and his wife Sharon, were hit with $1.7 million in tax debts from 2008 and 2009. Ozzy and Sharon paid off the sum a week after learning about it and owned up to their mistake.
"You have to be on top of your own business affairs," Mama Osbourne tweeted. "You can't rely on anyone but yourself. My fault...lesson learned."
But what's even more shocking than her consistent tax evasion? Before her rise to fame, Kimmy used to work for tax preparers at H&R Block. True story.
After failing to pay taxes on $700,000 of income for 2007 and 2008, the "Lean Back" rapper was sentenced to four months in prison and hit with a $15,000 fine for failure to pay taxes.
In 1990, the IRS notified country legend Willie Nelson he owed close to $17 million in tax debt. To assist with the payments, the singer signed over the profits to his not-so-subtly-titled 1992 album, The IRS Tapes: Who'll Buy My Memories? to the IRS.
The album generated nearly $3.6 million and he later paid off the full balance.
Since 2009, Uncle Sam has claimed the Illmatic rapper owes more than three million in back taxes.
When reports of an outstanding six million tax bill surfaced in early 2013, TheUrbanDaily.com asked the MC if he wished he'd been more business-minded. "No, I don't have any regrets," Nas said. "Your mistakes, when you go back to look at them, are just moments of being human...I love those points when I didn't do well because that meant I was just a human."
Marc Anthony is another famous repeat offender here. After the Latin singer paid $2.5 million in back taxes to get out of the red in 2007, he was forced to unload another $3.4 million to the IRS just three years later. The hefty sum was linked to unpaid taxes on his Long Island mansion.
Luckily, he got it all figured out. Bravo, Marc!
Despite millions of records of sold, the music legend faced a $1.1 million debt to the Feds in April 2012 thanks to unpaid taxes from 2010.