For the rich and famous, it's all fun and games 'til the money runs out. Even the most
accomplished Hollywood stars have been known to squander their fortunes away while they're
still in the spotlight.
Whether it's because of back taxes, excessive spending habits, or a few bad investments,
these celebrities hit the jackpot … and then watched it all disappear.
Lindsay Lohan
It's no secret that things haven't been easy for Lindsay Lohan over the last decade. There
was once a time when the star was a coveted actress with leading roles in the most well-received
teen comedies of the decade, including Mean Girls and Freaky Friday. In 2004, she even
took a dive into the music industry, and her first album, Speak, debuted at No. 4 on the
Billboard 200 charts. At the time, she made millions and covered just about every entertainment
magazine on the shelves.
"Shake your tailfeather, or shake it like a Polaroid picture?"
"Shake it like a Polaroid picture!"
Unfortunately, her legal issues rose as quickly as her fame. Between multiple DUIs, a high
profile arrest for theft, and other erratic behavior, the young star soon had trouble
landing lucrative roles and became more infamous than famous. Her 2007 flick I Know Who Killed
Me was laughed at by the press and her 2012 comeback The Canyons amounted to nothing more
than a poorly received softcore adult film masquerading as a drama. After allegedly failing
to pay rent and posing in Playboy for some cash, the IRS seized her bank account, claiming
she owed hundreds of thousands of dollars in taxes. Though Charlie Sheen allegedly loaned
her $100,000 to pay off some of her debts, she supposedly still owed another $100,000
before her mother lost their family's home to foreclosure.
Her net worth is now reportedly about $500,000, for which she can thank a gig as Lawyer.com's
spokeswoman, but that's a far cry from the massive wealth she'd acquired before things
spiraled out of control.
"Ugh. It's not funny!"
Tionne 'T-Boz' Watkins
Bankruptcy isn't crazy, sexy, or cool. Though TLC is one of best-selling girl groups in
history, their careers have been tarnished by financial hardship. For a time, Tionne
"T-Boz" Watkins, Lisa "Left Eye" Lopes, and Rozonda "Chilli" Thomas, were millionaires,
but it was short-lived. Really short-lived.
Even Watkins herself admitted to The Guardian:
"I will never forget the day we were millionaires for literally five minutes. Because the check
was written to us and we had to sign it over."
Their first bout of bankruptcy happened in the late '90s after their first two albums
made LaFace Records over $100 million. Then, T-Boz experienced crippling health issues
and found herself in more financial trouble in 2011. While Chilli managed to amass a $10
million net worth, partly thanks to her solo VH1 reality series, T-Boz filed for bankruptcy
twice. She reportedly owed creditors over $750,000, but only took in $11,700 per month.
Her catalog of multi-platinum records made her just $1,200 a month in royalties.
In 2017, she re-teamed with Chili for TLC's comeback tour and self-titled fifth album,
so perhaps things will start to turn around for the rapper-singer sooner than later.
Mike 'The Situation' Sorrentino
Jersey Shore's muscly meatball Mike "The Situation" Sorrentino has a bigger situation on his hands
than simply being short on cash. He's also facing potential jail time for tax evasion.
While the reality TV star was busy fist-pumping on his hit MTV series, he reportedly pulled
in a whopping $2.5 million per season. Unfortunately, he failed to pay taxes on nearly $9 million
of his earnings from the show's last two seasons, and the IRS moved in on him for his failure
to pay Uncle Sam.
Sorrentino's financial woes have been painfully documented on the revival series, Family Vacation.
Throughout the series, he shrugged about downsizing his car from a custom Ferrari, squirmed at
the cost of engagement rings, and was the butt of more than a few jail-time jokes.
"Dude. Prison's no joke."
His net worth is now estimated around $300,000, but, considering he's facing $250,000 in fines,
it could be cut down even more before it's all said and done.
"I did my best to better myself, become 'Better and not bitter.'"
"I'm trying my best to, um, continue to take on challenges and continue to move forward."
Aaron Carter
He may have beaten Shaq, but Aaron Carter isn't beating the IRS. The musician was once
teen royalty. His singles like "I Want Candy" and "Aaron's Party" pulled in millions before
he finished puberty. Carter was also a part of a love triangle that defined the early
aughts, when Hilary Duff and Lindsay Lohan were supposedly fighting for his affection.
Unfortunately, whoever was managing the then-teenager's finances made some major mistakes.
"When I was about 15 years old, my mother and father were my managers and you know they
were pulling at me left and right and all of a sudden they were divorced."
In 2009, Carter was slapped with a million-dollar tax lien from the IRS from bills dating back
to 2003.
"I had to file a Chapter 7 bankruptcy to protect my parents from going to prison for mismanaging
my finances."
By the time he was hit with the bill, he wasn't pulling in nearly the kind of cash he'd been
making before, and he ultimately filed for bankruptcy in 2013, claiming to have just
over $8,000 in assets and $60 in cash. According to TMZ, he owed over $2 million, including
a $31,000-plus American Express bill and over $1.3 million owed to the IRS.
Though Carter managed to reach a deal with the IRS in 2014, he's been very open about
being over $150,000 in debt.
"I'm sitting here in a f**king apartment, because I can't keep money in my bank account."
As of 2018, however, Carter has reportedly overcome some of his personal woes, so perhaps
he can turn his money matters around soon as well.
Teresa Giudice
This Real Housewives of New Jersey star spent a stint in the slammer for her money mismanagement
issues. She and her husband, "Juicy Joe," were caught for mail, wire, and bankruptcy
fraud, which added up to both jail time, and more than $400,000 in restitution.
The Giudices reportedly managed to pay off half of their restitution by 2016, just in
time for Joe to buy Teresa a brand new Lexus as a get-out-of-jail present. Due to their
restitution payment schedule, though, they're pretty much only allotted enough cash to pay
for food, shelter, and other necessities while Joe serves out his portion of the sentence
and faces deportation when he's done. The good news for the Giudice family is that they've
got a new reality show all lined up for when they move to Italy, so perhaps the Old Country
will offer them a fresh start.
Heidi Montag and Spencer Pratt
The Hills lovebirds Heidi Montag and Spencer Pratt may have high net worths, but that means
nothing when you're blowing through millions.
The reality TV couple has admitted to squandering their six-figure paychecks, which they reportedly
earned for various staged paparazzi shoots, public appearances, and their leading roles
as MTV's favorite villains.
"It was every single night we were taking 10 people to Wolfgang's Cut in Beverly Hills
and ordering $3,000 bottles of Screaming Eagle."
Speidi ended up wasting the vast majority of their fortune on everything from her extreme
plastic surgery binge to his strange crystal obsession, and the pair had to move in with
Pratt's parents for the last few years. When rent is zero, you can scrape by on almost
nothing. But with a brand new baby, things aren't going to be cheap.
Shad 'Bow Wow' Moss
If you've forgotten about Bow Wow, the charming young rapper who dropped the "Lil" infront
of his name when he grew up, you might recognize him from being roasted online. The once-rich
star, who raked in millions for flicks such as Like Mike and The Fast and the Furious:
Tokyo Drift, was caught posting stacks of someone else's money online with the caption
"Liquid cash." He was also dragged by fans for pretending he had chartered a private
flight and for editing himself into a picture with Tupac and Dr. Dre and passing it off
as real. In other words, Bow Wow's lux-looking social media is apparently totally fake.
For the last few years, Bow Wow has been having some real financial problems. According to
TMZ, the star owed nearly six figures in back taxes. He reportedly fell behind on his $300,000
business loan, owed $100,000 to a tour bus company, got his Lamborghini repossessed,
and was being sued for the $25,000 repossession fee. Debt collectors were also allegedly trying
to shake the star down for more than $283,000, which he owed for leasing a Ferrari in 2008.
During a 2012 child custody case, Bow Wow admitted he was pulling in just $4,000 a month
and had only $1,500 in his bank account. To make matters worse, in 2016, his series CSI:
Cyber was unceremoniously cancelled. That bites.
Stephen Baldwin
There aren't too many people who can get away with not paying their mortgage for six years,
but Stephen Baldwin was one of them. The Apprentice veteran was finally fired by his bank after
allegedly failing to pay his $7,000 a month mortgage and having an estimated $1.1 million
in debt, and Baldwin's house was foreclosed and auctioned off in early 2017.
Baldwin has a history of financial problems. In 2012, he was charged after failing to file
his New York state tax returns for multiple years and had to pay $300,000 in back-taxes
to avoid jail. He ultimately filed for bankruptcy in 2009 after owing more than $2.3 million.
While Stephen Baldwin may not be as successful as his brother Alec Baldwin, he still found
significant success in films like The Usual Suspects and Bio-Dome. Unfortunately, he's
snagged less roles in recent years and seems to have had a falling out with his more famous
sibling as a result of their political differences, so he probably can't call him up for some
cameo work on Saturday Night Live right about now.
"Yes, Alec, you do a brilliant Trump, baby. Now you got a gig for the next eight years!"
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