These Millionaires Lost it All at Least Once

The late 1980s and early 1990s were Hammer time. In 1991, the rapper was worth an estimated $33 million and well on his way to become one of the world’s richest rappers. However, in 1996 he filed for bankruptcy after having blown his money on a staff of 200, a multimillion-dollar mansion, a private jet, helicopters, flashy cars, thoroughbred horses and lawsuits. According to Bankrate, the man who gave us Hammer pants is now worth about $1.5 million.

Michael Jackson’s spending habits were as legendary as his moonwalk. A string of very expensive lawsuits ate into his fortune too and, according to Billboard, he was about $500 million in debt when he died in 2009. However, his estate has been raking in the money, making him the top-earning dead celebrity with a current net worth of about $500 million.

According to the Daily Mail, Nicolas Cage once had a fortune of about $150 million. He owned numerous properties, including castles. He also spent hundreds of thousands of dollars on flashy cars, exotic animals, art, comic books and a dinosaur skull that turned out to be stolen. Hefty unpaid tax bills left him deeply in debt, he faced foreclosures on some of his homes and was forced to sell some of his treasures. Today the actor’s net worth is about $25 million.

In 2014, TMZ reported that Rihanna was suing her accountant. The reason? At the beginning of 2009 she had $11 million but her accountant gave her bad advice. By the end of 2009 she was worth $2 million, while her expenses had doubled.

She bounced back, though, and is now worth around $250 million. Almost losing it all because of her accountant makes Rihanna living proof that there are some financial terms everyone should know.

According to GoBankingRates, Mike Tyson earned $700 million through his boxing career but filed for bankruptcy in 2003. How did he lose it all? Lavish spending, a stint in prison for rape, a costly divorce, unpaid tax bills and, of course, retiring from boxing and losing his main source of income.

He’s since found that a career change is one of the best things to do after retirement. His acting roles and two memoirs have helped to bring his net worth back up to $3 million.

In the 1980s, Kim Basinger was one of the biggest stars in Hollywood. By the end of the decade she was so rich that she bought an entire town. However, in 1993 she pulled out of a film project, was sued for millions she didn’t have and filed for bankruptcy. Her acting career has gone from strength to strength since then and the Oscar-winning actress is now worth $40 million, according to Celebrity Net Worth.

Burt Reynolds was one of the biggest stars of the 1970s and early 1980s, earning $10 million a year, according to Vanity Fair. However, a lavish lifestyle – including spending $100,000 on toupees – combined with a string of bad investments, a declining career and a very expensive divorce led him to file for bankruptcy in 1996. He’s had to sell of many of his assets, including movie memorabilia, and is now worth around $5 million.

At the height of his fame in the 1980s, Gary Coleman earned $64,000. Numerous health problems and legal troubles drained his bank account and in 1998 he was working as a security guard. In 1999, E! News reported that the former child star had filed for bankruptcy. He was virtually broke when he died in 2010.

50 Cent may count among the stars who made more money from business than from their day jobs. In 2015, the rapper was reportedly worth around $155 million. That same year, though, he filed for bankruptcy, citing debts of around $32.5 million, according to Verdict. Numerous lawsuits were given as the main reason for his bankruptcy. He has since paid back most of his debt.

Elizabeth Holmes founded blood-testing company Theranos in 2004, when she was 19. She was soon the star of the tech world and by 2014, Forbes listed her net worth as $4.5 billion. In 2016, however, the magazine adjusted this to 0. Holmes not only lost her fortune when the company was accused of running inaccurate tests. She also lost her reputation and has been charged with fraud.

Bjorn Borg dominated tennis in the 1970s and became the first player to win more than $1 million in prize money in a single season. However, in 1989 his sportswear company went bankrupt. He almost went personally bankrupt too when the taxman of Sweden – definitely not one of the world’s top tax havens – pursued him for $40,000 in back taxes. He narrowly avoided bankruptcy again in 1997, according to The Guardian, and in 2006 had to auction off his trophies and memorabilia.

Toni Braxton first filed for bankruptcy in 1998. According to Gulf News, her debts were the result of smaller-than-expected royalty checks and a lavish lifestyle. She bounced back but in 2010 she filed for bankruptcy again. The singer now has an estimated net worth of $10 million.

Willie Nelson is one of the most notorious celebrity tax cheats. In 1990, according to Rolling Stone, the taxman seized the country legend’s assets, saying he owed $32 million. He eventually released the album The IRS Tapes: Who’ll Buy My Memories to help settle the bill.

Crime doesn’t pay. However, in the case of Bernie Madoff, it paid for a little while. In 2009, the stockbroker and his wife were worth about $126 million. After his Ponzi scheme came crashing down and he was sent to jail, his assets were recovered and used to reimburse some the people he had defrauded. Bankrate now estimates his net worth at minus $17 million.

Boris Becker used to be one of the world’s wealthiest tennis players. However, he paid millions of dollars in a divorce settlement and a settlement with a model he had a child with.

He also lost millions in bad investments and in 2017 he was declared bankrupt. The Telegraph reported in 2018 that the former Wimbledon champion’s trophies were being auctioned to help pay his debts.

Aaron Carter was 7 when he started his career and before he turned 18, he had made over $200 million, according to The Huffington Post. After he turned 18, however, the younger brother of Backstreet Boys’ Nick Carter learned that his parents hadn’t managed his money all that well and that he owed more than he owned. He filed for bankruptcy in 2013.

Movie directors have one of the jobs that pay shockingly less than you think. Francis Ford Coppola made a fortune in the 1970s. However, in 1992 the Los Angeles Times reported that he had filed for bankruptcy for the third time since 1993, all because of a 1982 box office flop. Wise investments since then have meant that the director is now worth an estimated $321 million.

Chuck Feeney is one of those millionaires who won’t leave their kids much money.

He used to be one of the richest people in the United States but, as The Irish Times reports, he gave away more than $8 million. Today he lives in a rented apartment and is known as the James Bond of philanthropy.