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We often watch mega-rich celebrities with their mansions, fashionable clothes, and jet-setting ways with envy. However, managing the finances isn’t so easy for some that have risen to the top, just to watch the bank account slip through their fingers like sand.

Kanye West is one example of a rapper/artist that has seen the ease at which debt can take over a luxurious lifestyle. In 2016, West announced in a Twitter rant that he was $53 million in debt due to millions spent on cars, armored SUVs, jewelry, travel, and multiple homes.

According to CNBC, he may be on his way to a comeback because his apparel brand Yeezy has become a billion-dollar empire. The partnerships and negotiations with Adidas and Gap, to name a few, have many hoping it’s safe to say West will be just fine.

Other celebs have not been so lucky. Check out the list of celebrities that once had it all and now struggle to pay the bills.

Nicolas Cage – Current Net Worth: $25 Million

Cage was at one time one of Hollywood’s biggest stars. The Gone in 60 Seconds star had a net worth of around $150 million in the late ’90s to early 2,000’s. However, big spending leads to a big loss. According to Insider, Cage purchased so many homes, cars, and rare items that his finances suffered, and then, to make matters worse, he owed the IRS more than $6 million for failing to pay his 2007 taxes. Cage has since sold many of those super rare artifacts, including a one-of-a-kind comic book just to make ends meet.

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Michael Jackson – Current Net Worth: $7 Million

The net worth of Michael Jackson has been contradictory over the years. At the time of his death, executors estimated his net worth to be around $7 million, but the IRS said his net worth was closer to $1.2 billion. Strange… but what we do know for sure is near the end of his life, Jackson was $400 million in debt. With purchases like the Neverland Ranch, his unmatched music catalog, and unpaid bills to lawyers, agents, and publicists, Jackson was in hot water. In fact, the final tour he announced shortly before his death was planned to help him dig his way out of the debts, but the superstar never made it to the stage.

MC Hammer – Current Net Worth: $2 million

He took the world by storm in the early 1990s and performed one of the most recognizable one-hit wonders today. In 1991, Hammer’s net worth was approximately $33 million, but his wild spending on luxury vehicles, a 40,000 square foot mansion, and a staff of more than 200 put the singer in debt totaling $13.7 million. Hammer declared bankruptcy in 1996, according to Powered by Orange. By 2011, he was working to regain his financial status, working with a reported “eight technology companies.” He’s also taken to the stage and toured in 2019 for those die-hard fans.

Burt Reynolds – Current Net Worth: $3 Million

The famous movie star of the ’60s, ’70s, and ’80s at one time was making $10 million per year, but by the mid-’90s was forced to file bankruptcy due to lavish spending. Reynolds owned a 153-acre ranch in Florida, properties in Arkansas, California, Florida, Georgia, and North Carolina. He owned a private jet, a helicopter, several sports cars, and 150 horses. It’s reported Reynolds spent more than $100,000 on toupees. After an expensive marriage and expensive divorce to Lonnie Anderson, Reynolds was unable to pay debts on a $3.7 million loan, among others, for a total of $10 million in debt.

Willie Nelson – Current Net Worth: $25 Million

Nelson is arguably one of the most unforgettable singer/songwriters in history, and we all know how much he loves smoking marijuana, but money problems have plagued his career. In 1990, Nelson owed a staggering $16.7 million in federal taxes. After a lawyer negotiated his debt down to $6 million, he still couldn’t pay and ended up losing everything. According to Heavy.com, the government seized Nelson’s country club, recording studio, ranch, more than 20 other properties in four states, and most of his instruments, recordings, and memorabilia. In anticipation of the raid, Nelson hid his famous guitar, Trigger, at his daughter’s house and walked away with it in the end.

Charlie Sheen – Current Networth: $10 Million

The 52-year-old former bad boy of Hollywood was once making $1.8 million per episode of Two and a Half Men but lost it all when he lost his cool. According to Debt.com, Sheen is more than $12 million in debt, including mortgages, legal fees, and taxes. He owes the IRS $5 million alone, and a lavish lifestyle of overspending led to more than $300,000 owed to American Express, but most of those millions, he admits, have gone to drinking, drugs, and partying.

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Sources: CNBC, Insider, Powered by Orange, Heavy.com, Debt.com