Aside from unique jobs, adoring fans, and fame and fortune, celebrities have one thing in common with most Americans: They dread tax season. No one likes paying taxes, including these famous Hollywood stars. Like most Americans, celebrities overcome their anxiety and file tax returns right on time. However, celebrities are just as prone to making the same tax return sins as everybody else.
These celebrity tax cheats scammed the IRS out of millions of dollars. We’ll meet one of Hollywood’s most successful leading men (page 7), an Oscar-winning director (page 10), and a singer you might have forgotten about (page 13).
15. Lauryn Hill
- How much she owed: $1 million
The former member of the hip-hop group The Fugees had IRS trouble stemming from income from 2005 to 2007. The singer didn’t pay taxes on $1.8 million she earned from four companies she owned. She eventually settled her $1 million tax bill, but she served prison time and had to pay a $60,000 fine.
Next: A rapper commits the worst tax sin.
12. Fat Joe (TIE)
- How much he owed: $1.1 million
Two run-ins with the IRS led to a seven-figure tax bill for the rapper Joseph “Fat Joe” Cartagena. He committed the most egregious tax sin of all by not filing returns in from 2008 to 2010 and again in 2014. The feds stuck him with a $1 million bill, and he also paid off a $100,000 New Jersey tax lien before that.
Next: Unpaid taxes are just one of the hits this man has to his name.
12.Lionel Richie (TIE)
- How much he owed: $1.1 million
Given that he’s responsible for a string of musical hits, Lionel Richie probably didn’t have any trouble coming up with the money he owed the IRS. In 2012, the feds tagged him with a $1.1 million tax bill for not paying his taxes in 2010. He paid up and his problems disappeared.
Next: Back taxes were only part of his problems.
12. Ja Rule (TIE)
- How much he owed: $1.1 million
The IRS tracked down the former star rapper in 2011 and made him pay $1.1 million, but that was just part of his legal troubles at the time. Prosecutors charged him with attempted illegal gun possession in addition to the tax problems.
Next: An entertainment couple with tax problems.
10. Ozzie and Sharon Osbourne (TIE)
- How much they owed: $1.7 million
The Black Sabbath singer and his TV host wife landed on the IRS’ radar in 2011. The agency tagged them with a $1.7 million bill for unpaid taxes in 2008 and 2009, making the couple some of the biggest celebrity tax cheats ever.
Next: She learned there’s no way to outrun the IRS sleuths
10. Lindsey Vonn (TIE)
- How much she owed: $1.7 million
Lindsey Vonn posts fast times on the ski slopes as a world and Olympic champion, but she couldn’t outrun IRS sleuths. The government agency made her pay $1.7 million in back taxes in 2012. Vonn’s success on the slopes and her many endorsement deals helped her quickly pay off her debt.
Next: An action movie star, and one of the biggest celebrity tax cheats.
9. Robert Downey Jr.
- How much he owed: $2 million
He stars in Iron Man and Avengers movies now, but times weren’t always so good for Robert Downey Jr. Spending wildly on drugs and alcohol put him $2 million in the hole to the IRS. When he got clean and got his career back on track, he repaid his debts. He erased his debts but his old tax bill makes him one of Hollywood’s biggest celebrity tax cheats.
Next: Tax and debt problems dog this talented artist.
8. Annie Leibovitz
- How much she owed: $2.48 million
Annie Leibovitz is a photographer to the stars, and like the other people on this list, she is one of the worst celebrity tax cheats around. She skipped paying $2.1 million in federal taxes from 2004 to 2007, and New York state hit her with a $383,895 tax bill. Leibovitz is no stranger to debt problems. She faced a 2009 lawsuit for not paying back a $15 million loan.
Next: This comedian is on the right side of the IRS these days.
7. Chris Tucker
- How much he owed: $2.5 million
His movie releases are spread out now, but in the 1990s, Chris Tucker starred in hits such as Friday and Rush Hour. He made a lot of money, but he still had tax problems. Reports he owed $14 million to the IRS were wrong, but he paid back $2.5 million and squared his debts in 2014.
Next: The IRS tax bill was not a scene ripped from one of his movies.
6. Martin Scorsese
- How much he owed: $2.85 million
It sounds like a scene from one of his mobster movies — a man shows up on Valentine’s Day to collect a debt. Yet this was real life for Oscar-winning director Martin Scorsese, who got a call from the IRS on Feb. 14, 2011. Luckily, he had plenty of money from his storied movie career to pay what he owed.
Next: Our next person on the list completely ignored IRS obligations.
5. Al Sharpton
- How much he owed: $4.5 million
He’s not an actor or a singer, but Al Sharpton is well-known and he is one of the biggest celebrity tax cheats around. Not only is he a tax cheat, he willfully neglected to pay what he owed IRS. His National Action Network didn’t pony up its federal taxes, just one of many alleged indiscretions over the years.
Next: A singer for whom tax debt is just one problem
4. R. Kelly
- How much he owed: $4.8 million
A huge bill from the IRS for unpaid back taxes makes R. Kelly one of the biggest celebrity tax cheats we’ve ever seen. The singer at one time owed $5 million total. Even after he paid back $3.6 million there was $4.8 million left on his ledger thanks to interest and fines.
Kelly knows financial and legal troubles very well. His $3.5 million mansion auctioned for less than $1 million when he didn’t pay the mortgage, and sexual misconduct allegations against him are another big problem.
Next: Remember him?
3. Marc Anthony
- How much he owed: $5.9 million
The singer Marc Anthony is in the headlines less these days now that he isn’t married to Jennifer Lopez anymore. He’s familiar with headlines of another sort, however, and they aren’t good. Three separate bills for back taxes totaled $5.9 million, making him one of the biggest celebrity tax cheats ever.
Next: Two dubious accolades for our next celebrity.
2. Nicolas Cage
- How much he owed: $14 million
Nicolas Cage has at least two dubious accolades to his name. He is one of the worst actors of all time, and one of the biggest celebrity tax cheats in history. He has movies such as Bangkok Dangerous and The Wicker Man to thank for the former, and crazy spending habits to thank for the latter. Cage’s story is just one of many lessons in money management we can learn from celebrity tax cheats.
Next: Somehow, Cage is not the worst.
1. Wesley Snipes
- How much he owed: $17 million
Back taxes. Jail time. So-so movies. Wesley Snipes knows about all three. The actor never tried to hide his income, he just flat-out refused to pay his taxes. And he owed a lot, which is why he is No. 1 on the list of celebrity tax cheats.
When the IRS came calling, a judge ordered him to pay $17 million in taxes and penalties. Snipes served three years in prison, too. As for the iffy movies, well, at least Major League and White Men Can’t Jump made us laugh.
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