Nicolas Cage, or Castor Troy if you’re a Face Off fan, has had a remarkable fall from grace in recent years. Between 1996 and 2011, Mr. Cage was worth a whopping $130M from films such as Gone in Sixty Seconds ($20M paycheck), Nation Treasure ($20M paycheck), Snake Eyes ($16M paycheck) and Windtalkers ($20M paycheck). In fact, he’s ranked as one of the highest paid actors of all time! Rumor has it he made $40M in the year 2009 alone.
So what happened? Unfortunately as his paychecks increased, so did his spending habits. And he wasn’t just buying nice cars (although there were plenty of those). At one point, Cage bought a 67 million year old dinosaur skull for $300,000 to add to his collection of dinosaur skulls. He purchased two Bahamian Islands just south of Nassau for $7M, a Lamborghini that once belonged to the Shah of Iran for $450K, a $1M Ferrari Enzo and a Rolls Royce, among other luxury vehicles. His 12-bedroom yacht set him back a cool $20M, his private Gulfstream jet was no small change and his fifteen properties around the world each cost at least $10M.
Eventually, Cage was forced to foreclose on several properties and his money manager countersued him, costing him millions. Although the lawsuits have been settled, Cage is still working on rebounding from his epic losses.
Fortunately, he has starred in big budget films over the past few years and has sold many of his assets to help pay off his debts.
Although 50 Cent, or Curtis Jackson as he would be in court, claims that filing for bankruptcy in 2015 was “strategic” and a protective move after he was slapped with a $5M lawsuit for releasing a sex tape featuring his rap rival Rick Ross’ ex-girlfriend without her consent, we aren’t so sure we believe him.
He claimed that he felt he had a bulls eye on his back where people would take advantage of his wealth by suing him without cause, or using him to get cash. Filing for bankruptcy was his way of preventing any further attacks.
While Forbes estimated his net worth at $155M, Jackson’s lawyer claimed he only had $4.4M in the bank when the $5M lawsuit was filed against him.
In the summer of 2016, Jackson was ordered to pay out $17M to the audio equipment company, Sleek Audio and $6M to Lastonia Leviston, Rich Ross’ ex and the subject of the sex tape.
Whether his bankruptcy was smoke and mirrors or not, the media still covered it as legitimate bankruptcy and mismanagement of his earnings since his breakout in the early 2000s.
At her lowest point, Courtney Love had $4000 to her name and was forced to move into a rented apartment with her daughter, Francis Bean. When Kurt Cobain died in 1994, Love inherited over $200M, and the publishing rights to all of Nirvana’s music. Over the years, she lost almost all of it due to lawsuits, including one with the remaining members of Nirvana over the band’s unreleased material.
Love was able to get out of debt by selling 25% of her shares in the Nirvana material. Love claims she has shielded the songs from misuse in a number of endorsement offers from brands like Coca-Cola, KFC and a condom manufacturer. Come As You Are suddenly has a whole new meaning.
It’s a classic tale of talent gone awry. Dennis Rodman divorced his third wife, who left him along and took their 9 and 10 year old children when his endorsement opportunities were rolling in. He neglected to pay child support or spousal support for a number of years, racking up almost $1M of unpaid fees. His ex-wife sued him for misconduct, and his lawyer fees skyrocketed while his endorsements plummeted.
Rodman is known for his crazy lifestyle of parties, drugs, women and spending money. At one point, he was charging money to make appearances at events just to make ends meet. By the time the lawsuit was resolved, Rodman was unable to pay his lawyers so they worked pro bono in order to help him settle his finances.
Brendan Fraser, best known for his role in The Mummy franchise, pleaded with a Connecticut court to reduce his annual alimony fees of $900K claiming that he no longer made enough money to justify the price tag. When Fraser first divorced his ex-wife, Afton Smith in February of 2009, he was making millions at the box office. We’re guessing $900K felt like pocket change when The Mummy raked in half a billion dollars worldwide. So what went wrong? How did Fraser fall flat?
According to reports, Fraser injured his back while attempting to clear debris during a cleanup after Hurricane Sandy. His injury was so severe that it required corrective surgery and intense physical therapy rehabilitation. Eventually, he was forced to admit that he could no longer do his own stunt work, which was a huge part of his appeal. Bottom line, he claimed that his medical concerns severely impacted his earning potential.
His legion of fans have gone so far as to sign a petition to get him back in the game (because we all know Hollywood loves a good comeback story!), but so far the studios won’t bite.
Heidi Montag & Spencer Pratt
Heidi Montag and Spencer Pratt have a lot of regrets. The married couple, who rose to reality TV fame from their roles on MTV’s The Hills, once had a net worth up $10M. Now, they’re living with their parents and exclaiming their regrets in a string of interviews.
Montag recently told media she had breast augmentation surgery to remove her six F breasts that she had done back in The Hills days. She said the breast augmentation surgery helped with the pain she was in on a daily basis. Size F on her small frame is unnatural and often results in back issues. Montag has reportedly had other surgeries on her face and body and the before and after photos really speak for themselves.
Pratt and Montag claim they were spending money like it was growing on trees in the years after their MTV fame. Pratt would tip valets hundreds of dollars, spend $15K on a night out, gifted his friends thousands of dollars to purchase vehicles and designer goods. Montag has a self-proclaimed obsession with designer handbags, on which she reportedly blew up to $1M. Pratt also purchased millions worth of crystals.
The most bizarre part of their story isn’t Montag’s breast augmentation or Pratt’s crystals. It’s the fact that the couple reportedly spent what remained of their fortune in anticipation of the Mayan apocalypse back in 2012. They were so convinced that the end was coming that they went all out and purchased everything and anything they wanted to ensure no dollar was wasted. We’re sure they woke up the morning after with significant buyers remorse.
Mike Tyson reportedly earned $300M over the course of his boxing career. His lavish lifestyle and constant legal battles cost him so much that he now struggles to pay his IRS fees.
Although he has always maintained his innocence, Tyson was convicted and served time for rape in the 90s. After his release, he attempted a boxing comeback and fought Evander Holyfield in what would become his most infamous fight when he bit his opponent’s ear. Tyson’s boxing license was soon revoked, and his lifestyle of violence and partying resumed.
Tyson filed for bankruptcy in 2003 and retired from boxing in 2005. He has been arrested several times since when he fought a photographer at LAX and assaulted two motorists.
Tyson has managed to preserve his status in Hollywood by doing cameos in comedy shows and movies such as The Hangover. His most bizarre foray into entertainment of late has been his show on Animal Planet called “Taking on Tyson”, which shows him caring for, speaking to and protecting his first loves: pigeons. At first glance, it isn’t obvious whether it’s a comedy show or not, but it is clear that Tyson is definitely living in his own world.
In 2009, the youngest of the four Baldwin brothers filed for bankruptcy. He owed about $1.2M on his mortgage in New York City and more than $1M in taxes at the time. His credit card debt was also through the roof. In a shocking police report, it was revealed that a homeless man who was invited to stay at Stephen’s home was arrested on drug possession and drug dealing charges. Stephen claimed he just thought he was doing a good deed.
The actor had mild success as an actor over the years, from his appearance in “The Usual Suspects” to various appearances on reality TV shows, but his paychecks were irregular and couldn’t cover his lavish, celebrity lifestyle. Compare that to the eldest of the Baldwin brothers, Alec Baldwin, who has found immense success on the show 30 Rock and most recently on the SNL stage. We can imagine what it would be like to sit around the Baldwin family dinner table.
One of the best-selling recording artists of the 90s, Toni Braxton rose to superstardom with hits like “Unbreak my Heart”, six Grammy wins and a loyal fan base. But according to Braxton, she hit a serious low when she was forced to file for bankruptcy in 1998, spiraling into a deep depression.
The singer blamed her debt of $5M on bad business contracts and extravagant tour costs, but other expenses such as Gucci hand bags, grand pianos and thousand dollar gowns were also to blame. Braxton shared her woes publicly at the time, appearing on Oprah and doing interviews with major magazine and newspaper publications. It appeared that she might rebound when she remarried and had children of her own.
In 2010, Braxton filed for a second bankruptcy, this time citing over $15M in debt with less than $10M in assets. She owed money to Atlantic Records, the IRS, Wells Fargo and the state of Georgia for her taxes. Her case took over 5 years to resolve, leaving Braxton with very little money and the hope of one day reviving her singing career.
When you think of celebrities and tax evasion, Wesley Snipes’ name is bound to be the top of your list. Snipes was famously arrested and served three years in prison for tax evasion from 2010 through to 2013. The actor was found guilty of not paying up to $15M of taxes to the government for his earnings from 1999 to 2001. His lawyers argued that Snipes’ tax advisors, who were also convicted, misled their client into thinking he didn’t need to pay taxes in the first place.
While in prison, Snipes tried to appeal his sentence to the Supreme Court, but his appeal was refused and he was ordered to finish his sentence. Ironically, he was released and put on house arrest two weeks before tax day in 2013.
Michael Vick has had a bumpy ride. The former Atlanta Falcons quarterback landed in jail on dog-fighting charges in 2008 with $20M in debt to various parties including the Falcons, his former agent and a Canadian financial institution that forced him to file for bankruptcy in 2008. His career and his reputation were flat lined; he served his time and then eventually slowly put himself back together again.
According to reports, Vick paid back every dime that he owed in an effort to restore his relationships and his reputation. His new deal with Philadelphia is $100M over six years with $35M guaranteed if he gets injured. In 2011, Vick resigned with Nike, who dropped him when he was arrested. Numerous other endorsements have come through now that he is back on track. Well played.
Arguably the most famous Playboy model of all time and a celebrity icon in her own right, Pamela Anderson has been in significant trouble with the IRS for tax evasion. She reportedly owned up to $1M in unpaid taxes, causing her to go into debt and file for bankruptcy. That and she had two messy divorces that cost a lot in legal fees.
She has reportedly been in disputes with multiple contractors who built her home in California, but she claims the dispute did not put her in debt and that she is within her legal rights to take them to court.
Anderson hasn’t been in the spotlight for her career as an actress for many years, but she continues to get paid to make appearances at events and parties.
A man infamous for parachute pants and living large, MC Hammer blew his $30M fortune quickly and without abandon, forcing him to file for bankruptcy. How did MC Hammer go bankrupt? Let us count the ways.
He reportedly had a staff of up to 200 people who he paid on salary, and rolled with a 40-person entourage at all times that cost him $500K per month. He built a 40,000 square foot home for $30M that included added touches like gold-plated gates, multiple swimming pools, a baseball diamond, tennis courts, a recording studio, a 40-seat theatre and rare antiques.
He purchased a number of million-dollar thoroughbred horses, helicopters, Lamborghinis, a private jet and other transportation options to fill his 17-car garage.
He wasn’t just a big spender. Hammer was embroiled in multiple lawsuits related to copyright infringement charges. His most notable court battle was with Rick James, who claimed Hammer ripped off the bass riff from his icon song “Super Freak” for the notorious “Can’t Touch This” song. Hammer lost in court and was forced to give over a significant portion of the royalties.
Hammer filed for bankruptcy in 1996 with a debt of over $13M, sold his estate and became an adorned minister. How did MC hammer go bankrupt? He made a laundry list of terrible financial decisions.
Kim Basinger was a Bond girl and Batman’s girlfriend before she was struggling to book roles and going bankrupt. In one bizarre, impulsive move, Basinger purchased a town called Braselton, Georgia for $20M with a vision to turn it into a tourist attraction theme park. When she bought it, the town had over 500 resident who were less than pleased with her plans. Her vision was never realized and Basinger was thrown into a number of financial difficulties shortly thereafter.
In 1993, the producers of the film “Boxing Helena” sued Basinger when she withdrew from her contract to play the lead, costing her over $8M in damages. That same year, the state of Georgia liquidated her holdings in Braselton for a substantial loss forcing her into bankruptcy.
Basinger has appeared in a number of films recently in small roles, but the story of her buying an entire town on a whim is arguably her greatest act.
DMX is famous for his string of hits in the late 90s and early 2000s, his raspy growl, east coast aggression and club bangers. He found great success in music and film, and seemed to have it all. Unfortunately, once the money started to pour in, so did his misdemeanor charges, drug use, excessive partying and violent ways. DMX has filed for bankruptcy three times in the span of two decades in the spotlight, most recently in 2016 with a reported $2M owed to creditors and his New York home in the balance.
The rapper has 15 children under the age of 10 with 9 different women. He owes over $300K in child support charges, and $1.4M in spousal support, not to mention over $1M of debt to various financial institutions.
In recent interviews, DMX claims he has $0 to his name and apparently does not own the rights to any of his music. His drug use and drug abuse have skyrocketed in recent years, leading to a reported overdose late last year. His drug use has been ongoing since he first broke out on the rap scene, but drugs have taken over his life and his finances as the years progressed.