21 A-List Celebs Who Had Serious Tax Issues

Taxes are a basic requirement of adult life, and while it's believed that celebrities are just like the rest of us, quite a few of them have been found to have neglected to pay their taxes entirely or on time.
The fact that well-known actors, singers, TV hosts, and athletes are wealthy is widely known. Additionally, income taxes on such high-income levels are staggering. Many famous people employ a small army of accountants to help them manage their finances, particularly taxes. It seems nonetheless that they don't always get the greatest counsel.
Some famous people avoid paying their taxes for years. These debts turn serious whenever the Internal Revenue Service (IRS) lodges a tax lien. Celebrities who fail to pay their taxes on time in some cases even risk going to jail.
Some of the names on this list might surprise you. Even without any prior legal troubles, tax evasion can make a well-known entertainer the subject of media attention. You'll find 21 well-known celebrities listed below who ultimately owed the IRS taxes ranging from tens of thousands to millions of dollars.

#1 Christie Brinkley

Source: Byrdie

On her $30 million Long Island property, supermodel Christie Brinkley was hit with $531,000 in back taxes in 2011.  When the IRS filed a lien on her, Brinkley vowed to reply right away and fully settle the debt.

#2 Dionne Warwick

Source: WTVM

Dionne Warwick, a musician with dozens of hits to her credit, is hardly a person one would anticipate declaring bankruptcy. But in 2013, when she owed the federal government almost $7 million in taxes, she did just that.
According to reports, Warwick, who currently resides in Brazil, has been negotiating with the state of California to settle her obligations.

#3 Floyd Mayweather Jr.

Source: The Cold Wire

According to a federal tax lien filed by the IRS, boxer Floyd Mayweather Jr. owes a stunning $22.2 million in taxes from 2015.
After his bout with Conor McGregor, Mayweather Jr. petitioned the IRS for a delay in filing his taxes. In 2015, he asserted to have paid the IRS $26 million.

#4 Ja Rule

Source: Ticketmaster

Ja Rule and his wife, Aisha Atkins, were reported to owe the IRS almost $3 million in delinquent taxes in April 2021. Ja Rule reportedly made the full payment later in June.
Ja Rule had financial issues before; in 2011, he was sentenced to 26 months in prison for failing to submit income tax forms to the government.

#5 Judy Garland

Source: Biography

In 1964, actress and singer Judy Garland was issued a $4 million tax bill. She had previously skipped paying taxes in 1951 and 1952.
She lost her home to the IRS after she was unable to pay the tax debt, forcing her to live in hotels until her passing in 1969.

#6 Lauryn Hill

Source: Biography

After failing to pay $1.8 million in taxes from 2005 to 2007, singer Lauryn Hill entered a guilty plea to the charges.
Her outstanding balance increased to about $2.3 million after state and federal taxes from 2008 and 2009 were taken into account. Her three-month prison sentence in Connecticut began in June 2013.

#7 Lil Wayne

Source: Rap Mais

In 2012, Lil Wayne had almost $7 million in unpaid taxes, but the rapper was short on funds because of a troubled recording deal.
Unbelievably, fellow rapper Jay-Z was instrumental in getting Lil Wayne out of trouble. During a 2018 concert in Chicago, Lil Wayne openly honored Jay-Z.

#8 Lindsay Lohan

Source: IMDb

Lindsay Lohan, a former child star, has had plenty of legal run-ins. Lohan was said to have underpaid $100,000 in taxes in 2017.
Charlie Sheen allegedly assisted Lohan in 2012 with the repayment of an extra $100,000 in tax-related debt.

#9 Martha Stewart

Source: Entrepreneur

TV star Martha Stewart was sentenced to pay $220,000 in overdue taxes on a New York state property before her run-in with the law for insider trading in 2004.
According to reports, Stewart initially declined to pay the whole amount since she insisted she didn't spend much time on the home.

#10 Martin Scorsese

Source: The New York Times

Did you know that director Martin Scorsese, who is known for classic Movies like Taxi Driver and Goodfellas, owed $2.85 million in taxes in 2011?
Before this, Scorsese owed about $2.1 million in back taxes from 2002, 2003, and 2004. He fully satisfied those debts.

#11 Mary J. Blige

Source: Biography

The singer Mary J. Blige owes the IRS over $1.2 million in back taxes after she failed to file her tax returns for 2016 and 2017.
It was discovered that Blige owed the IRS a total of closer to $6.5 million between the years 2008 and 2016.

#12 Mike "The Situation" Sorrentino

Source: Silver Screen Beat

Mike "The Situation" Sorrentino of the Jersey Shore received a two-year prison term after admitting to filing false tax returns for around $9 million in January 2018.
The reality star and his brother Mark were initially charged with conspiring to defraud the US and violating tax laws in 2014.

#13 Nicolas Cage

Source: IMDb

The actor Nicolas Cage has spent a lot of money throughout his career, including buying a dinosaur skull, two castles, and more than a dozen homes. Is it any surprise, then, that in 2009, the IRS filed a $6.2 million tax lien against him?
As if that weren't enough, Cage later that year received a second $6.7 million tax lien from the IRS.

#14 O.J. Simpson

Source: The Irish Sun

Most people recognize O.J. Simpson with his high-profile murder trial, but as of April 2021, the former athlete still owes $1.4 million in overdue taxes.
It will be difficult to obtain the money, though. For the foreseeable future, Simpson is being held in a Nevada prison after being found guilty of kidnapping and armed robbery.

#15 Pamela Anderson

Source: Rotten Tomatoes

Pamela Anderson, a Baywatch star, was the target of two tax liens. The first was in 2010 when she owed outstanding personal income taxes totaling just over $493,000.
Anderson was confronted with a second tax lien for an extra $370,000 two years later, in 2012.

#16 Sinbad

Source: CBS News

Sinbad reportedly owed the IRS almost $8 million and the state of California $2.3 million in taxes back in 2013.
The comedian allegedly owed $32,000 to Bank of America and over $375,000 to American Express as part of his purported credit card debt.

#17 Sophia Loren

Source: Biography

Sophia Loren, an Italian actress, spent time in jail in 1974 over a tax issue. Her accountants determined that her tax bracket required her to pay out 60% of her income, despite the government claiming that it was 70%.
The allegations against Loren were dropped 39 years later; after all, the amount she had filed in 1974 was accurate.

#18 Stephen Baldwin

Source: Rotten Tomatoes

After being accused of not submitting his income tax returns from 2008 to 2010, Stephen Baldwin was detained in 2012 on suspicion of tax evasion. He was thought to owe more than $350,000.
Baldwin, though, entered a not-guilty plea. Baldwin was given five years by the judge to settle the amount; he may avoid probation if he did so within a year. By 2014, Baldwin had paid off his loan entirely.

#19 Teresa & Joe Giudice

Source: ABC News

The Real Housewives of New Jersey's Teresa and Joe Giudice were charged with 39 charges of bank fraud, making false statements on loan applications, making conspiracy to commit mail and wire fraud, and bankruptcy fraud in 2013.
The Giudices initially entered a plea of not guilty, arguing that they were singled out for prosecution due to their notoriety. However, the two ultimately agreed to a guilty plea deal that mandated jail time for them both.

#20 Wesley Snipes

Source: Rotten Tomatoes

Between 1999 and 2004, when he made a staggering $40 million, actor Wesley Snipes did not pay any income taxes. Snipes was found guilty on three misdemeanor counts as a result of failing to file his federal taxes.
Snipes volunteered to pay $842,000 toward his debt but was nonetheless given a three-year prison term. He finally had to pay the IRS what he owed in 2020, which came to $9.5 million.

#21 Willie Nelson

Source: Biography

Willie Nelson settled a $16.7 million tax debt with the IRS in 1993, making it one of the most well-known tax disputes in music history. His accountants had established tax havens, but the IRS declared them invalid, resulting in a hefty fine.
Although Nelson's attorney was able to reduce his debt to a more manageable $6 million, the government nonetheless seized and auctioned off his property. Fortunately, most of his belongings were bought by family and friends who then swiftly returned them to him.
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