Reality stars and rappers.
Actors and artists.
For one reason or another these celebrities avoided paying the big bucks.
Reality stars seem particularly susceptible to tax troubles, so we're kicking it off with
"Jersey Shore" star Mike Sorrentino, better known as "The Situation."
The Staten Island-born star rose to fame in 2009 with the debut of the addictive MTV reality
series, which ran until 2012.
Two years after the show ended, Mike was indicted on charges that he had avoided paying taxes
on $8.9 million in income.
Per Forbes, both Mike and his brother, Marc Sorrentino, were accused of filing false tax
returns and committing fraud.
They were also alleged to have used their companies to evade taxation, using company
money for personal expenses like expensive cars and clothing, claiming them as legitimate
business expenses.
In January 2018, Mike and his brother pleaded guilty to the charges, and he was sentenced
to eight months in federal prison.
A few months later, he shared his thoughts on his approaching jail time with Us Weekly.
He explained,
Mike started his sentence a year after pleading guilty and was freed eight months later.
Aside from the jail time, the reality star was also sentenced to two years of supervised
release, a $10,000 fine, and 500 hours of community service.
"Is prison like it is in 'Goodfellas'?"
"Oh, um…"
Long before he was involved in the infamous Fyre Festival debacle, Ja Rule got himself
involved in a different kind of scandal — one of the tax fraud variety.
In March 2011, the rapper pleaded guilty to three counts of failing to file a tax return
and agreed to pay over $1.1 million in tax debts, plus added penalties.
Prior to his sentencing, the star suggested that he had already paid millions in taxes
and had simply fallen short.
He confessed on "MTV's RapFix Live", stating,
He was sentenced to 28 months in prison for the offense but actually served more time.
That period was tacked on to a two-year sentence he was already facing for a 2007 weapons charge.
He was eventually released from prison two months earlier than his anticipated July 2013 release.
Sadly, Rule's tax trouble didn't end there.
In 2021, the rapper and his wife, Aisha Atkins, were accused of refusing to pay more than
$3 million in federal taxes, according to Radar.
The money in question was reportedly owed from the years 2005 through 2010 and 2012
through 2017.
Naturally, one of Rule's most famous foes, 50 Cent, took the opportunity to poke fun
at the situation on Instagram.
Sharing a screenshot of the Radar report and with laughing emojis in the caption, he wrote,
In the '90s, Wesley Snipes found massive success in Hollywood with films like "White Men Can't
Jump," "Demolition Man," and "Rising Sun."
Unfortunately, the actor seemingly didn't file taxes after 1998.
Per Fox News, the government claimed he made around $13.8 million during that time and
racked up at least $2.7 million in back taxes.
Per People, in 2008, the actor was convicted of three counts of willfully failing to file
tax returns and was handed a three-year sentence.
He was also fined $5 million for failing to file taxes, though at that time he was acquitted
of five additional charges that included tax fraud and conspiracy.
In 2010, an appeal he'd submitted against the charges was denied and he entered federal
prison that December.
During an appearance on "Larry King Live" that same year, Snipes suggested he felt his
case had been mistreated by the media.
"They claimed that, uh, there was a certain number of, uh, that was owed and that number
has slid all over the place."
He added,
He ended up doing a little over two years of that sentence and was released in April 2013.
Seven years later, he told The Guardian that his experience in jail gave him a new appreciation
for spending time with loved ones.
In December 2012, the youngest brother of the Baldwin acting dynasty, Stephen Baldwin,
was arrested and charged with failing to pay his taxes.
He pleaded not guilty at the time of his arrest.
The actor was alleged to have amassed a $350,000 debt after neglecting to pay New York state
taxes from 2008 to 2010.
Per CNN, three months later, the actor pleaded guilty and confessed to having failed to file
his taxes for three years.
However, in a statement given while leaving court, he attempted to provide some explanation
for his wrongdoings, saying,
The actor added that he was excited to get his debt paid off.
Surprisingly, although he faced up to four years in prison, Baldwin's plea deal didn't
require any jail time.
Instead, he had to pay $300,000 in back taxes, dodging the interest and penalty fees that
would have made him liable for $400,000.
The actor paid off the last of his debts in April 2014, a month before he found himself
in trouble with the law again – this time for driving with a suspended license.
In June 2012, singer Lauryn Hill — best known for her work with hip-hop group the
Fugees before going solo — was charged with failing to file over three years of income taxes.
Per MTV, the IRS estimated she'd earned more than $1.6 million within that period.
The following month, the musician pleaded guilty to three counts of failing to file
tax returns.
Hill was sentenced in May 2013, and she was very vocal with the judge about her case.
Per CNN, the star pointed out the amount of money her music had made for other people
and insisted that she lived modestly by comparison.
She stated,
The singer famously addressed her legal troubles in a lengthy tirade on Tumblr, in which she
continued to plead her case about living a humble lifestyle.
Hill added that she made a conscious decision to step away from the mainstream after experiencing
a crisis that made her feel devalued by the industry and belittled by the media.
She noted,
She was given a three-month prison stint alongside three months of house arrest.
Additionally, she was asked to pay what she owed on top of a $60,000 fine.
The singer served her time and was released a few days early in October 2013.
Most people are familiar with media mogul Martha Stewart's legal troubles involving
insider trading in 2004, but the icon has also found herself in some tax trouble, too.
This time, it involved a complicated case where Stewart owed taxes to the state of New York.
According to The New Yorker, the star's main residence — and site of many a photo shoot
in her Martha Stewart Living magazine — happened to be in Westport, Connecticut.
However, she also owned two properties in New York in the '90s — a cottage in East
Hampton and an apartment in Manhattan.
Stewart didn't deny owning property in the state in 1991 and 1992.
Instead, she claimed that neither was a permanent residence and that both dwellings were undergoing
renovations that rendered them uninhabitable.
When Stewart was eventually tried for tax evasion years later in 1998, she was unable
to deny residency due to some surprising pieces of evidence.
For starters, the jacket copy for her books published in those years read,
Further damning were photographs of both properties in her own magazine that satisfied the judge
as to them being fully furnished, habitable, and lived in.
Per The New York Times, it was eventually ruled that she pay back over $200,000, plus
penalties and interest.
Stewart reportedly paid that figure back in full.
Country legend, Willie Nelson, got himself into so much trouble with the IRS that he
had to put out an entire album to help repay the debt!
As reported by The New York Times, back in 1990, the free-spirited musician was found
to have accrued a tax debt estimated to be around $32 million — the largest ever owed
by an individual at that time.
He subsequently had multiple properties and belongings like touring equipment, master
tapes, and gold and platinum records seized by federal agents, according to Rolling Stone.
"Obviously I have to start off by letting you know, I'm not a cop."
"I'm not either."
"Okay, good."
After his assets had been taken into possession, the IRS charged him a debt of $16.7 million.
By 1993 that figure was brought down to $9 million, and after paying $3 million of that
debt off, he decided to put out a two-disc collection to help pay the rest off.
"The IRS Tapes: Who'll Buy My Memories" was released in 1992 and was pieced together from
35 years worth of seized recordings that the IRS gave him access to.
In 1995, Nelson reflected on the experience with surprisingly fond memories.
He told Rolling Stone,
Power vocalist Toni Braxton made it big in the R&B world in the '90s with songs like
"Un-Break My Heart" and "Breathe Again."
Sadly, over the years she has found herself in trouble with the IRS not once, but twice.
In 2018, The Blast reported that the star owed over $700,000 to the IRS and the state
of California after four tax liens were filed against her.
A year later, she was again revealed to owe a massive amount of back taxes with E! News
reporting that the IRS had filed a lien against the star for over $340,000.
Meanwhile, the state of California had filed its own tax lien against Braxton for $116,000.
The almost half-a-million dollars that Braxton reportedly owed were dated back to 2017, which
the outlet noted was a financially successful year for the singer.
The performer had finished out her The Hits Tour while starring in the reality series,
"Braxton Family Values."
As of this video, it's unclear how much of her debts she has currently paid off.
Sadly, financial issues are nothing new for Braxton, as the star has filed for bankruptcy
twice in her life — first in 1998 and again in 2010.
Two years after her second bankruptcy filing, she told "20/20" that while she was prone
to overindulgence, the nature of her early record contracts also left her with little
to live off of.
"A hundred and seventy million in sales and you got $1,972?
Is that right?"
"I did. That's right.
That's true."
Fat Joe began his rise to fame in the '90s, making a name for himself in the rap scene.
Unfortunately, by 2012, he'd started making headlines for something other than hit songs
when he pleaded guilty to tax evasion.
Per The Hollywood Reporter, the musician had reportedly made almost $3 million in just
two years and was found to subsequently owe over $700,000 in unpaid taxes to the federal government.
At the time, his defense attorney, Jeffrey Lichtman, told the New York Post,
Six months later, the rapper was sentenced to four months in prison for tax evasion and
served time between August and November 2013, per Rolling Stone.
Six years later, he reflected on how his penalty made him reevaluate his prior beefs, telling
"The Breakfast Club,"
"Like, I knew when I came out of jail I had to squash my s--- with JAY-Z.
Squash my s--- with 50 Cent and any loose ends I had out there."