Easy come easy go could be the motto for some celebrities when it comes to money. Some have made millions for just one job, but ended up in bankruptcy for lavish spending, or, as is the case for many, not paying the IRS its due.
And the IRS, as the saying goes, does not play. Failing to meet tax liabilities can result in jail time, as is the case with actor Wesley Snipes. Many end up going the bankruptcy route to get relief.
Where does the money go? Lavish lifestyles that include expensive cars, high-priced mansions, state of the art jets, jewelry, and legal fees to keep themselves out of the slammer for things such as DUIs, assault, and assault and battery.
But America especially is a funny place and is more apt to forgive and forget than probably any other place on the planet. Celebrities that blow their money often end up with best-selling books and cameo appearances in the movies, on TV, and at clubs. They may lose their cash flow, but they are still making enough to live fairly well.
And often, their friends bail them out. Recently, singer/actor Tyrese Gibson in a tearful social media post claimed he was broke due to legal fees and child support while his custody case over his daughter raged on. Actors Will Smith and (wife) Jada Pinkett Smith apparently bailed him out – for now – with a $5 million infusion of their own money.
What does he need $5 mil for? Another car? A trip to Barbados to sort out his feelings?
15. Mike Tyson Blew So Much Money…
At one point, Mike Tyson was the most feared man in boxing, and the richest. During the first 18 years of his boxing run, he earned about $400 million. But this guy is one who couldn’t buy his way out of trouble. He went to prison after being found guilty of assault. Then he declared personal bankruptcy… where did all that money go? The New York Times called Tyson a “cash machine to himself,” and revealed he lived a lavish lifestyle, spending money on everything from jewelry to Siberian tigers. And of course when it came right down to it, he also failed to take care of tax liabilities… he owed the IRS alone more than $17 million by the time he filed for bankruptcy. Eventually he sold his Connecticut mansion to cover some of the debt he had accrued – that’s right – in addition to blowing hundreds of millions of dollars, he owed millions to creditors. Tyson lives more modestly now, and makes money with guest appearances on game shows and in movie and TV cameos.
14. Lena Headey of ‘Game of Thrones’ Claimed She Was Broke
How do you star in one of the most popular shows on television and claim you only have $5 to your name? Lena Headey may play a queen on Game of Thrones, but at one time she was living on the edge of poverty. No details were ever revealed as to how she ended up broke in the middle of a top-rated TV show, but it might have something to do with a nasty divorce, an ugly custody battle and taking a $450,000 hit on a real estate deal. Headey was so broke, she tried to get a judge to give her half of a tax return filed by her and her ex-husband to cover living expenses. Well, that was 2013. By April 2014, it looks like she got back on her feet. According to Forbes, she bought a fixer upper in Sherman Oaks, Calif., for $790,000. And by mid 2015, she gave birth to her second child, a daughter.
13. Rihanna Sang ‘Diamonds’ While Seeing Red
Not that long ago, the stunning lady from Barbados who once stole Chris Brown’s heart and had the ears of millions around the world was seeing red in her bank account, despite millions of dollars in record sales. Rihanna lost more than $9 million in one year, and she says it happened due to bad advice from her accountant. According to a lawsuit she filed against the accountant, she started 2009 with $10 mil in her bank account, but by the end of the year she had less than $2 mil left, mostly due to a purchase of a Beverly Hills home that turned out to be a dud filled with mold and leaks. The accountant claimed that Rihanna actually was going broke because she spent huge amounts of money on jewelry and designer clothes. In the end, the court sided with Rihanna and ordered the accountant to pay her $10 million. Funny thing… the same year RiRi was suffering financial woes is the same year then boyfriend Chris Brown beat the crap out of her.
12. Chris Tucker Was Once The Highest Paid Actor In Hollywood…
He was considered a comedic genius, able to stand next to the likes of the late great Richard Pryor and Eddie Murphy. Indeed, after Rush Hour 3, he was considered the highest paid actor in Hollywood… he made a whopping $25 million for that film. Life was good. He bought mansions and even had his own very popular comedy club in Atlanta. Then TMZ discovered Tucker owed more than $12 million in back taxes. Oh-oh. Better call Jackie Chan, but even he couldn’t help his good friend and co-star kick his way out of trouble with the federal monkey on Tucker’s back. He had to sell two of his Florida mansions and one in Los Angeles, and his comedy club went down the pooper, too. In 2012, he made a bit of a comeback, appearing with Robert DiNiro in Silver Lining Playbook. He currently does comedy clubs around the world.
11. Lady Gaga Blew Wad On Clothing
She is famous for different looks, but those looks apparently cost Lady Gaga millions. It was back in 2009 when the songstress launched her Monster’s Ball tour. The costumes were elaborate, to say the least. According to reports, the tour, and more specifically the costumes, left her $3 million in debt. And, she said she had no idea until the media started reporting that she had spent that much and was rumored to have financial woes. But she followed that by saying she didn’t really pay attention because money isn’t important to her. In the end, the tour paid off after an 18-month run. But it was touch and go for a minute, so much so that her own father was worried. She told the New York Daily News: “I remember I went home and I was with my dad and he said ‘I don’t understand. “Bad Romance” is out. You are all over the radio. Everyone is talking about you and you don’t have a pot to piss in’.” Her plan was to get the attention of the chairman of Live Nation, Arthur Fogel, and she did. And in the end, Live Nation wrote her a $40 million check and the tour was a huge success.
10. Abby Lee Miller Danced Her Way Into Financial Trouble… And Prison
Abby Lee Miller was one of the reality stars that took the popular Dance Moms to the top. But the no-nonsense mom was dancing to a different tune away from the cameras. Her rising star – and fortune – dropped like a lead balloon when she pleaded guilty to bankruptcy fraud in 2016. According to the Washington Post, Miller, the dance studio owner in Pittsburg where Dance Moms was taped, allegedly tried to hide hundreds of thousands of dollars in income that she made for appearing on the Lifetime show. In addition, she reportedly smuggled more than $120,000 in Australian currency into the U.S., according to Fox News. The next step: prison. That came after her bankruptcy judge saw her on TV and realized that she was probably not as broke as she claimed to be. “I realized there is a lot of money coming into this plan, this case, and it hasn’t been disclosed,” the judge said. Miller began her one-year sentence in July.
9. Lindsay Lohan Asked Charlie Sheen For Money
Lindsay Lohan was a Disney star, featured in The Parent Trap and Freaky Friday. She went on to make a slew of movies before she was 18. But her behavior, and thus her bank account, kept taking hits. A lot of folks thought she had found her way back after Mean Girls, but the arrests and negative situations continued to pile up. Lindsay’s career derailed. She had drug and partying habits that went on, despite even being locked up at least once. By 2012, she was bankrupt. Part of her problem was the IRS, which had put a freeze on any assets she still had. According to the IRS, she owed $250,00o. Things got so tough for Lohan that she asked Charlie Sheen for $100,000. Ouch! Even as late as 2014, she still had money woes. She tried to party at 1 Oak in New York City, but the club turned down her credit card, and her friends had to pool their money to pay the $2,500 tab. Maybe she paid off the IRS and had her liens released, which would mean she would be able to receive royalties again because she celebrated her last two birthdays (30 and 31) in Greece.
8. Pamela Anderson Had To Sell Home She Spent Big Bucks On To Decorate
You can run like a bae on Baywatch, but you can’t run from the IRS. Ask Pamela Anderson. The former Playboy bunny, like a lot of stars, seemed to forget that the IRS wants it share, especially when you get big. Anderson stayed in the spotlight for quite some time for two reasons: her smokin’ hot bod and her penchant for rock stars. She once married Tommy Lee and she also did a walk down the aisle with Kid Rock. None of that kept her from being examined by the IRS. The IRS wanted to know why she wasn’t paying taxes since she obviously had money from all the work she was having done, and where did she get more than a mil to spend on decorating her house? Not only did Anderson have to declare bankruptcy, she had to sell the very house she spent all that money to cover her debt. She seems to have made a recovery, as she was recently seen in Paris dressed to the nines and looking like she had just come off a new round of procedures.
7. Nicolas Cage – Not Much Of A Shark When It Comes To Money
When you make about $15 million per movie and you do a few a year, it’s easy for the money to add up. In fact, according to sources, Nicolas Cage made about $150 million between 1996 and 2011. That’s pretty sweet. Well, that is so unless you spend it foolishly. Welcome to Nicolas Cage’s world. In recent years, he’s faced financial woes, mostly due to his crazy – and we do mean crazy – spending habits. Over the years, he has bought quite a collection of cars and exotic jewelry, but that’s not the crazy part. He’s also spent money on a shark, a crocodile, two king cobras, a dinosaur skull, a collection of shrunken heads, and a pyramid tombstone in New Orleans. Oh, and then there’s the IRS, which placed a multi-million dollar lean on his mansion in New Orleans. He also lost two homes – one in California and one in Nevada- to foreclosure. Cage has made a bit of a recovery in the last couple of years, working on about a dozen movies. Maybe he’ll be more thrifty this time around.
6. ‘Unbreak My Heart’ Diva Toni Braxton Breaks The Bank, Twice
Toni Braxton came onto the scene with a bang when she released “Unbreak My Heart,” an emotional ballad that became the favorite to cry along with when getting over a break up. She skyrocketed to fame and fortune. But 15 years later, she was contemplating posing nude for Playboy to help pay her bills. She told ABC News that she decided not to do it because of her two sons and other family members. What would they think? More importantly, though, how did she get where she had to declare bankruptcy? Braxton apparently had an addiction to – get this – houseware. We’re talking Faberge eggs, 1.000-thread sheets, and other household things, or as she called them, “girly things.” She also said that people don’t realize that record labels recoup what they spend to launch an artist and keep her in the limelight. Braxton, in fact, declared bankruptcy twice. She still performs and now also has a boyfriend who likes to treat her to nice gifts, such as a new car. That boyfriend is Birdman, CEO of Cash Money Records.
5. The Funny Willie Nelson IRS Story
Willie Nelson is an iconic pop/country singer who made the big time with songs such as “Beer for My Horses” (a duet with Toby Keith); “Mama Don’t Let Your Babies Grow Up to Be Cowboys” (with Waylon Jennings); “To All the Girls I’ve Loved Before (with Julio Iglesias); and “Always on My Mind,” which was a huge crossover hit. The only trouble was Nelson didn’t pay taxes on his earnings, and, you guessed it, the IRS came calling to the tune of more than $16 million. And back in the early ‘90s, that was a lot of money. Basically, the IRS took everything and he went bankrupt. Now the funny part… Nelson made an album called The IRS Tapes: Who’ll Buy My Memories? It was a hit, selling enough copies for Nelson to be able to pay off all of his debt in just three years. Nelson is doing just fine at 147 years old – no really… he’s actually 84. Dude still performs and in fact will be touring in 2018.
4. Johnny Depp May Need To Make Another ‘Pirate’ Movie
Johnny Depp came into the limelight as a young rebel cop on 21 Jump Street. His fan base grew over the years as he moved into movies and made a rep for himself as he excelled at roles where he played unconventional characters. And along with his bank account grew a penchant for spending money for… unconventional things. Rumor is nowadays that the Pirates of the Caribbean actor has a less than healthy cash flow. Odd (and expensive) expenditures include once paying $3 million to fire Hunter S. Thompson’s ashes out of a cannon. And recently he went through a very costly divorce from Amber Heard. Then there’s the #18 million yacht, 30K a month on wine, private jets, and a chain of Caribbean islands. Depp is reportedly suing his managers, claiming that they are responsible for his money woes. But the managers have struck back, saying Depp is on the edge of insolvency because he spends more than he makes. Ouch. That’s a lot of money gone down the pooper considering Depp’s fortune was once estimated at $400 million.
3. 50 Cent Lost So Much They Should Have Renamed Him Two Bit
Like a lot of hip hop artists, 50 Cent, aka Curtis James Jackson, rose from the streets to incredible popularity and riches. The Get Rich or Die Tryin’ rapper made 30 million in record sales and then made some investments, including Glaceau vitamin water, which was eventually sold to Coca-Cola for $100 million. But like so many of his peers that came from poverty, he spent most of those millions on a lavish lifestyle that included Rolls Royces, the very same mansion that Mike Tyson had to sell to get out of debt, and by handily giving away cash to family and friends. Wait, there’s more. 50 Cent became embroiled in lawsuits, most of which he lost, including one where he had to pay an ex-girlfriend millions after he released a tape of him and her after she had started a relationship with another rapper. He also got hit with a $17 million judgment for allegedly stealing a design for headphones, and he admitted at one point that he lost millions on the stock market. Now into film and TV, 50 Cent has a series called Power on Starz.
2. Curt Schilling’s Game Was A Big Loser
Curt Schilling led the Boston Red Sox to a World Series win, something the team hadn’t experienced in more than 80 years of baseball. He retired rich and famous. A gamer at heart, Schilling put together a deal to launch a spanking brand new gaming experience that he said would rival highly popular World of Warcraft. He even convinced the state of Rhode Island into investing a whopping $75 million into his plan that would include hundreds of jobs and eventually, revenue for the state. It failed within two years, putting those same hundreds out of work and failing to make its loan payment to Rhode Island to the tune of $1.1 million a pop. Schilling’s rep went down the pooper. By the time all the litigation and court battles were done, Schilling’s $50 million retirement fund was down to about $1 million. He got a job as a baseball analyst at ESPN, but eventually blew that too after making racially-charged comments on social media.
1. Donald Trump Not Really A Financial Guru
Before his uncanny presidential run, Donald Trump had a reality show called The Apprentice and a spinoff of it called The Celebrity Apprentice. People were given the impression he was a great businessman, a financial whiz if you will. But the truth is that between 1991 and 2009, he declared bankruptcy for businesses of his no less than six times. It’s no wonder he refused to release his tax returns during his campaign. According to Forbes and Money Crashers, when the Trump Taj Mahal went under, the debt load was more than $3 billion. Ouch. To help with the debt, Trump had to sell his Trump Shuttle (airline) and his personal yacht. In 2004, when he declared bankruptcy for Trump Hotels and Casinos, the debt load was $1.8 billion. That was the first time… he declared Chapter 11 again in 2009 for the same properties. Bottom line: Trump used American bankruptcy laws to salvage his business empire, and the kicker is, those heavy losses never affected his flamboyant lifestyle, as he never personally guaranteed any of his business ventures.
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