How These Celebs Blew a Massive Bag and Went Broke

In 2004, MJ’s financial advisers declared the “Thriller” legend was unable to repay a $70m loan to the Bank of America, according to the Independent. Despite being nearly broke, Michael Jackson was reportedly still living a lavish lifestyle, which only deepened his financial hole. In 2009, Jackson was set to perform at a planned concert residency in London to help with his growing debt. Unfortunately, the singer died in August before the tour could begin. At the time of his death in 2009, Jackson owed more than $500 million, according to court documents.

When T-Pain— real name Faheem Rashad Najm— hit the scene in the 2000s, he was making millions with his innovative autotune and r&b sound. At the height of his career, the singer reportedly had $40 million, but years later, Najm revealed he had to borrow money just to buy his kids Burger King. According to him, a “series of bad investments” and other bad spending habits caused him to go broke. Now, the “I’m Sprung” singer says he’s doing much better financially, making more money playing videos than he did making music. Good on you, T-Pain.

The athlete filed for bankruptcy in 2003 after years of financial struggles, according to the New York Times. Over his career as a heavy weight legend, Tyson reportedly earned $400m, but he spent around $400,000 a month to maintain his lavish lifestyle, according to court documents. “I have been in financial distress since 1998, when I was burdened with substantial debt to Showtime, taxing authorities, and parties to litigation,” Tyson said in an affidavit. “Since that time, although my fight income, various asset sales, and litigation recoveries have enabled me to pay a lot of my debt, I am still unable to pay my bills.”

The boxing legend and all his pigeons are in a much better place now, especially reportedly making millions on his last fight that no one can forget.

It’s hard to think that a musical icon like Dionne Warwick would ever run into financial troubles. But in 2013, she filed by bankruptcy, citing tax debt that dated back to 1991 of over $10 million. “Due to several consecutive years (the late ’80s through the mid-’90s) of negligent and gross financial mismanagement, Dionne Warwick has realized the current necessity to file personal bankruptcy,” her publicist, Kevin Sasaki, said in a statement. The case was dismissed in 2019.

Before 50 Cent— real name Curtis James Jackson III— became the “Power” mogul he is today, times were tough. In fact, in 2015, the New York rapper filed for bankruptcy. “Businesspeople will do that in a heartbeat before losing money,” he told the Guardian in 2020. “Because it means they have the ability to be secure and invest again.” Now, his net worth is estimated around $40 million.

The late, great Gary Coleman was once the highest-paid actor on TV. But in 1999, the “Diff’rent Strokes” star declared bankruptcy, according to Business Time. Just 10 years earlier, Coleman reportedly had $7 million, but after a series of legal battles and costly medical expenses, Coleman went broke. He later said he could “spread the blame” for his bankruptcy “from me to accountants to my adoptive parents, to agents to lawyers and back to me again.” He ended up working as a security guard and sadly never returned to acting. He died at age 42.

A shady record deal kept singer Toni Braxton in debt for a long time. “What happens is they give you advancement on the next record and then the next record,” she told ABC in 2015. “So you kind of stay in debt, in a sense.” In 1998, the singer filed for bankruptcy. Years later, Braxton would try to get back on track but after a series of health related issues forced her to cancel several shows, she couldn’t catch a break. She declared bankruptcy again in 2010.

After a hit like “U Can’t Touch This,” it’s not shocking that MC Hammer— real name Stanley Kirk Burrell— thought his millions would last forever. But after accumulating $70 million, he filed for bankruptcy in 1996. According to Blue Tree Savings, Burrell owed more than $13 million. He’s since bounced back from financial turmoil and is now a tech entrepreneur, often speaking at events about financial literacy.

In her last years, the jazz singer experienced financial hardships mostly stemming from the government’s attack on her and her rocky love life. At the time of her death in 1959, Billie Holiday only had $0.70 in her bank account, which equates to around $7 today. The singer also had $750 strapped to her leg, according to the Medium. She died without a will.

We all know the story of Wesley Snipes and his taxes, but in case you need a refresher, the actor failed to file his taxes for multiple years, and in 2008, he was convicted and sentenced to three years behind bars, according to Reuters. Since he was released from prison, Snipes has returned to acting and even was set to join the Marvel universe until his “Blade” reboot was scrapped.

Life for Grammy Award winner Marvin Gaye was going good until he filed for bankruptcy in 1976. Gaye is one of the most famous American musicians of all time, but he was reportedly behind on alimony payments to his first wife, Anna Gordy Gaye, according to Case Western Reserve. Gaye also owed money to the IRS and was behind on mortgage payments. At the time of his death in 1984, his estate was about $9 million in debt.

According to Money Nation, Rihanna went from having a net worth near $50 million to almost losing it all. In 2009, life for the “Umbrella” singer was hard. She began the year with around $11 million, and by the end, she had only $2 million. This was the same year she was assaulted by ex-boyfriend Chris Brown. In 2012, the cause of her financial woes was confirmed to be her accountant who wrongfully managed her money, according to the HuffPost. She won the lawsuit against Berdon LLP in 2012, and as we all know, she’s now a certified billionaire.

After an unforgettable run with the Chicago Bulls in the ‘90s, life for Dennis Rodman hasn’t been the same. In fact, he reportedly stopped paying child support, which added up to be $800,000. His lawyers came to his defense saying Rodman was broke and sick which is why he couldn’t pay off his debts. He was also accused of stealing a $2,000 amethyst crystal from a yoga studio and thousands of dollars’ worth of merchandise from different brands like Lululemon, according to the Bleacher Report. As of today, his net worth is around $500,000.

According to TMZ, the r&b singer owed the IRS $3.4 million in taxes from 2009 to 2011. Mary J. Blige also owed the state of New Jersey nearly $1 million in taxes at one point and was even sued for allegedly defaulting on bank loans worth over $2 million. “I owed so much money I never thought I’d ever get out of debt,” she said. And to make matters worse, a divorce from her husband meant Blige had to pay $30,000 per month in temporary spousal support from 2016 to 2018. Now, the “Family Affair” singer says she out of debt and living her best life.

In 1976, Rock and Roll Hall of Famer Isaac Hayes filed for bankruptcy after being in $6 million debt. He owed most of his money to the IRS after failing to file taxes. Hayes also attributed his lavish spending as a key reason for the filing. Eventually, he bounced back, making more music, writing a best-selling cookbook and even opening up two restaurants. At the time of his death in 2008, he was worth about $2 million.